NPASS Compound

Structure

NPC475849 OpenBabel07101718322D 31 34 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1902 -0.2750 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 -3.2604 2.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1264 2.1472 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 -4.1974 -1.7549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2162 -1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4635 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1687 -0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3168 -0.7620 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 -2.7293 -1.0747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3944 1.1472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4094 -0.3417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2604 0.6472 0.0000 C 0 0 2 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 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2604 1.6472 0.0000 C 0 0 0 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 11 25 1 0 0 0 0 12 22 1 0 0 0 0 13 3 1 1 0 0 0 13 17 1 0 0 0 0 14 4 1 6 0 0 0 14 19 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 0 0 0 0 22 28 2 0 0 0 0 22 30 1 0 0 0 0 23 29 1 0 0 0 0 23 31 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.3
Volume:	456.835
LogP:	5.262
LogD:	4.837
LogS:	-5.042
# Rotatable Bonds:	5
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	4.918
Fsp3:	0.96
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.745
MDCK Permeability:	4.7170426114462316e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.684

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	96.17919158935547%
Volume Distribution (VD):	1.924
Pgp-substrate:	3.057222366333008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	4.763
Half-life (T1/2):	0.342

ADMET: Toxicity

hERG Blockers:	0.606
Human Hepatotoxicity (H-HT):	0.294
Drug-inuced Liver Injury (DILI):	0.782
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.49
Carcinogencity:	0.043
Eye Corrosion:	0.019
Eye Irritation:	0.023
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: NPC475849

Natural Product ID:	NPC475849
*Common Name:**	(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-Methyl-2-((1Ar,4R,4As,7R,7As,7Bs)-1,1,4,7-Tetramethyldecahydro-1H-Cyclopropa[E]Azulen-4-Yloxy)Tetrahydro-2H-Pyran-3-Yl Isobutyrate
IUPAC Name:	[(2S,3R,4S,5R,6R)-2-[[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] 2-methylpropanoate
Synonyms:
Standard InCHIKey:	KYBCKZPKDGOQLN-PHSVILLSSA-N
Standard InCHI:	InChI=1S/C25H42O6/c1-12(2)22(28)30-21-20(27)19(26)14(4)29-23(21)31-25(7)11-10-16-18(24(16,5)6)17-13(3)8-9-15(17)25/h12-21,23,26-27H,8-11H2,1-7H3/t13-,14-,15+,16-,17-,18-,19+,20+,21-,23+,25-/m1/s1
SMILES:	CC1CCC2C1C3C(C3(C)C)CCC2(C)OC4C(C(C(C(O4)C)O)O)OC(=O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517303
PubChem CID:	44567062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1965654]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	9.0	%	PMID[486738]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	0.0	%	PMID[486738]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	>	20.0	ug.mL-1	PMID[486738]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	0.0	%	PMID[486738]

☑ 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 NPC475849 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	423
0.1-0.2	4039
0.2-0.3	13770
0.3-0.4	10127
0.4-0.5	6703
0.5-0.6	6297
0.6-0.7	1249
0.7-0.8	79
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC474266
0.9868	High Similarity	NPC216941
0.9342	High Similarity	NPC188793
0.8444	Intermediate Similarity	NPC474182
0.8372	Intermediate Similarity	NPC470009
0.8118	Intermediate Similarity	NPC474156
0.8111	Intermediate Similarity	NPC191915
0.8111	Intermediate Similarity	NPC151214
0.8065	Intermediate Similarity	NPC130792
0.7935	Intermediate Similarity	NPC252056
0.7931	Intermediate Similarity	NPC470657
0.7841	Intermediate Similarity	NPC31349
0.7826	Intermediate Similarity	NPC215570
0.7805	Intermediate Similarity	NPC279575
0.7738	Intermediate Similarity	NPC170595
0.7727	Intermediate Similarity	NPC471411
0.7727	Intermediate Similarity	NPC471410
0.7692	Intermediate Similarity	NPC235051
0.7684	Intermediate Similarity	NPC470030
0.7654	Intermediate Similarity	NPC470660
0.7654	Intermediate Similarity	NPC470659
0.7634	Intermediate Similarity	NPC57964
0.7634	Intermediate Similarity	NPC94582
0.7614	Intermediate Similarity	NPC290612
0.7604	Intermediate Similarity	NPC108227
0.7604	Intermediate Similarity	NPC472081
0.7604	Intermediate Similarity	NPC476838
0.7604	Intermediate Similarity	NPC476512
0.7604	Intermediate Similarity	NPC476839
0.7586	Intermediate Similarity	NPC29342
0.7586	Intermediate Similarity	NPC2572
0.7561	Intermediate Similarity	NPC472945
0.7561	Intermediate Similarity	NPC472944
0.7561	Intermediate Similarity	NPC308489
0.7553	Intermediate Similarity	NPC203434
0.7553	Intermediate Similarity	NPC156377
0.7553	Intermediate Similarity	NPC237071
0.7553	Intermediate Similarity	NPC238796
0.7532	Intermediate Similarity	NPC199937
0.7528	Intermediate Similarity	NPC64862
0.7526	Intermediate Similarity	NPC470029
0.7526	Intermediate Similarity	NPC310138
0.7526	Intermediate Similarity	NPC134967
0.7526	Intermediate Similarity	NPC114700
0.75	Intermediate Similarity	NPC18953
0.75	Intermediate Similarity	NPC70996
0.7474	Intermediate Similarity	NPC261372
0.7474	Intermediate Similarity	NPC472273
0.7474	Intermediate Similarity	NPC263674
0.7474	Intermediate Similarity	NPC58267
0.7449	Intermediate Similarity	NPC476837
0.7449	Intermediate Similarity	NPC97260
0.7449	Intermediate Similarity	NPC139181
0.7444	Intermediate Similarity	NPC472396
0.7444	Intermediate Similarity	NPC140446
0.7444	Intermediate Similarity	NPC43912
0.7439	Intermediate Similarity	NPC248427
0.7419	Intermediate Similarity	NPC475307
0.7412	Intermediate Similarity	NPC272841
0.7412	Intermediate Similarity	NPC177343
0.7368	Intermediate Similarity	NPC296936
0.7363	Intermediate Similarity	NPC470872
0.734	Intermediate Similarity	NPC175
0.734	Intermediate Similarity	NPC30687
0.7333	Intermediate Similarity	NPC472745
0.732	Intermediate Similarity	NPC41843
0.7317	Intermediate Similarity	NPC185419
0.7317	Intermediate Similarity	NPC184550
0.7294	Intermediate Similarity	NPC83108
0.7294	Intermediate Similarity	NPC214030
0.7292	Intermediate Similarity	NPC470591
0.7292	Intermediate Similarity	NPC278939
0.7292	Intermediate Similarity	NPC473555
0.7292	Intermediate Similarity	NPC471770
0.7292	Intermediate Similarity	NPC210157
0.7283	Intermediate Similarity	NPC131466
0.7283	Intermediate Similarity	NPC82955
0.7273	Intermediate Similarity	NPC212340
0.7263	Intermediate Similarity	NPC473065
0.7263	Intermediate Similarity	NPC93869
0.7263	Intermediate Similarity	NPC473064
0.7263	Intermediate Similarity	NPC473067
0.7263	Intermediate Similarity	NPC21897
0.7263	Intermediate Similarity	NPC6765
0.7253	Intermediate Similarity	NPC5943
0.7253	Intermediate Similarity	NPC213658
0.7253	Intermediate Similarity	NPC62202
0.7253	Intermediate Similarity	NPC110365
0.7253	Intermediate Similarity	NPC45833
0.725	Intermediate Similarity	NPC477758
0.725	Intermediate Similarity	NPC477754
0.725	Intermediate Similarity	NPC477759
0.725	Intermediate Similarity	NPC477760
0.725	Intermediate Similarity	NPC477761
0.7245	Intermediate Similarity	NPC475574
0.7245	Intermediate Similarity	NPC478181
0.7241	Intermediate Similarity	NPC472943
0.7241	Intermediate Similarity	NPC472951
0.7234	Intermediate Similarity	NPC473726
0.7234	Intermediate Similarity	NPC211845
0.7234	Intermediate Similarity	NPC256104
0.7234	Intermediate Similarity	NPC122083
0.7234	Intermediate Similarity	NPC182740
0.7229	Intermediate Similarity	NPC291228
0.7229	Intermediate Similarity	NPC308096
0.7222	Intermediate Similarity	NPC235402
0.7216	Intermediate Similarity	NPC157739
0.7204	Intermediate Similarity	NPC279329
0.7195	Intermediate Similarity	NPC471879
0.7188	Intermediate Similarity	NPC476510
0.7188	Intermediate Similarity	NPC142264
0.7188	Intermediate Similarity	NPC474297
0.7174	Intermediate Similarity	NPC281004
0.7172	Intermediate Similarity	NPC94919
0.7159	Intermediate Similarity	NPC473257
0.7158	Intermediate Similarity	NPC274588
0.7157	Intermediate Similarity	NPC472079
0.7143	Intermediate Similarity	NPC317019
0.7143	Intermediate Similarity	NPC215968
0.7143	Intermediate Similarity	NPC166250
0.7143	Intermediate Similarity	NPC155531
0.7143	Intermediate Similarity	NPC131365
0.7129	Intermediate Similarity	NPC165405
0.7129	Intermediate Similarity	NPC85670
0.7128	Intermediate Similarity	NPC293609
0.7128	Intermediate Similarity	NPC307167
0.7128	Intermediate Similarity	NPC59006
0.7128	Intermediate Similarity	NPC210759
0.7128	Intermediate Similarity	NPC473066
0.7128	Intermediate Similarity	NPC36372
0.7128	Intermediate Similarity	NPC229801
0.7125	Intermediate Similarity	NPC477751
0.7125	Intermediate Similarity	NPC477764
0.7125	Intermediate Similarity	NPC477752
0.7125	Intermediate Similarity	NPC477756
0.7113	Intermediate Similarity	NPC236580
0.7113	Intermediate Similarity	NPC470028
0.7113	Intermediate Similarity	NPC233649
0.7113	Intermediate Similarity	NPC304445
0.71	Intermediate Similarity	NPC34562
0.7097	Intermediate Similarity	NPC102725
0.7097	Intermediate Similarity	NPC228059
0.7097	Intermediate Similarity	NPC473472
0.7087	Intermediate Similarity	NPC208333
0.7087	Intermediate Similarity	NPC227879
0.7079	Intermediate Similarity	NPC148740
0.7079	Intermediate Similarity	NPC242771
0.7079	Intermediate Similarity	NPC100366
0.7079	Intermediate Similarity	NPC60018
0.7079	Intermediate Similarity	NPC202688
0.7079	Intermediate Similarity	NPC154043
0.7079	Intermediate Similarity	NPC164289
0.7079	Intermediate Similarity	NPC311642
0.7079	Intermediate Similarity	NPC102156
0.7071	Intermediate Similarity	NPC477172
0.7059	Intermediate Similarity	NPC469788
0.7059	Intermediate Similarity	NPC203974
0.7059	Intermediate Similarity	NPC186851
0.7059	Intermediate Similarity	NPC290247
0.7059	Intermediate Similarity	NPC176756
0.7059	Intermediate Similarity	NPC469787
0.7053	Intermediate Similarity	NPC167644
0.7053	Intermediate Similarity	NPC474835
0.7053	Intermediate Similarity	NPC277774
0.7053	Intermediate Similarity	NPC311246
0.7045	Intermediate Similarity	NPC117137
0.7045	Intermediate Similarity	NPC471216
0.7045	Intermediate Similarity	NPC471217
0.7045	Intermediate Similarity	NPC66766
0.7041	Intermediate Similarity	NPC292775
0.7037	Intermediate Similarity	NPC206601
0.7033	Intermediate Similarity	NPC266651
0.703	Intermediate Similarity	NPC469827
0.7021	Intermediate Similarity	NPC473542
0.7021	Intermediate Similarity	NPC65550
0.7021	Intermediate Similarity	NPC223143
0.7011	Intermediate Similarity	NPC252483
0.7011	Intermediate Similarity	NPC191345
0.701	Intermediate Similarity	NPC170527
0.7	Intermediate Similarity	NPC471761
0.7	Intermediate Similarity	NPC241959
0.7	Intermediate Similarity	NPC190418
0.7	Intermediate Similarity	NPC474253
0.7	Intermediate Similarity	NPC477285
0.7	Intermediate Similarity	NPC471760
0.7	Intermediate Similarity	NPC474346
0.7	Intermediate Similarity	NPC475820
0.7	Intermediate Similarity	NPC470070
0.7	Intermediate Similarity	NPC111582
0.7	Intermediate Similarity	NPC154452
0.7	Intermediate Similarity	NPC165069
0.7	Intermediate Similarity	NPC213737
0.7	Intermediate Similarity	NPC69953
0.7	Intermediate Similarity	NPC474284
0.7	Intermediate Similarity	NPC472744
0.699	Remote Similarity	NPC469826
0.699	Remote Similarity	NPC224414
0.699	Remote Similarity	NPC167044
0.6989	Remote Similarity	NPC33398
0.6979	Remote Similarity	NPC305418

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 NPC475849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	509
0.1-0.2	4129
0.2-0.3	3095
0.3-0.4	764
0.4-0.5	434
0.5-0.6	207
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6875	Remote Similarity	NPD8171	Discontinued
0.6813	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3669	Approved
0.6786	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1811	Approved
0.6552	Remote Similarity	NPD1810	Approved
0.6514	Remote Similarity	NPD8133	Approved
0.6484	Remote Similarity	NPD6928	Phase 2
0.6444	Remote Similarity	NPD4802	Phase 2
0.6444	Remote Similarity	NPD4238	Approved
0.6415	Remote Similarity	NPD6412	Phase 2
0.6396	Remote Similarity	NPD6940	Discontinued
0.6355	Remote Similarity	NPD6686	Approved
0.6283	Remote Similarity	NPD7328	Approved
0.6283	Remote Similarity	NPD7327	Approved
0.6264	Remote Similarity	NPD6115	Approved
0.6264	Remote Similarity	NPD6118	Approved
0.6264	Remote Similarity	NPD6114	Approved
0.6264	Remote Similarity	NPD6697	Approved
0.6237	Remote Similarity	NPD1779	Approved
0.6237	Remote Similarity	NPD1780	Approved
0.6228	Remote Similarity	NPD7516	Approved
0.6207	Remote Similarity	NPD2687	Approved
0.6207	Remote Similarity	NPD2686	Approved
0.6207	Remote Similarity	NPD2254	Approved
0.6203	Remote Similarity	NPD2267	Suspended
0.619	Remote Similarity	NPD8086	Approved
0.619	Remote Similarity	NPD8138	Approved
0.619	Remote Similarity	NPD8139	Approved
0.619	Remote Similarity	NPD8083	Approved
0.619	Remote Similarity	NPD8082	Approved
0.619	Remote Similarity	NPD8085	Approved
0.619	Remote Similarity	NPD8084	Approved
0.6174	Remote Similarity	NPD8294	Approved
0.6174	Remote Similarity	NPD8377	Approved
0.6154	Remote Similarity	NPD6116	Phase 1
0.6147	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD8276	Approved
0.6132	Remote Similarity	NPD8275	Approved
0.6121	Remote Similarity	NPD8379	Approved
0.6121	Remote Similarity	NPD8378	Approved
0.6121	Remote Similarity	NPD8033	Approved
0.6121	Remote Similarity	NPD7503	Approved
0.6121	Remote Similarity	NPD8296	Approved
0.6121	Remote Similarity	NPD8380	Approved
0.6121	Remote Similarity	NPD8335	Approved
0.6111	Remote Similarity	NPD3702	Approved
0.6104	Remote Similarity	NPD2269	Approved
0.6092	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6371	Approved
0.6075	Remote Similarity	NPD8081	Approved
0.6071	Remote Similarity	NPD371	Approved
0.605	Remote Similarity	NPD7507	Approved
0.6044	Remote Similarity	NPD6117	Approved
0.6026	Remote Similarity	NPD887	Approved
0.6026	Remote Similarity	NPD895	Approved
0.6026	Remote Similarity	NPD894	Approved
0.6026	Remote Similarity	NPD889	Approved
0.6019	Remote Similarity	NPD8393	Approved
0.6	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3198	Approved
0.5974	Remote Similarity	NPD904	Phase 3
0.5974	Remote Similarity	NPD905	Approved
0.5963	Remote Similarity	NPD8140	Approved
0.5963	Remote Similarity	NPD8307	Discontinued
0.5943	Remote Similarity	NPD1700	Approved
0.5902	Remote Similarity	NPD7319	Approved
0.5882	Remote Similarity	NPD7909	Approved
0.5862	Remote Similarity	NPD897	Approved
0.5862	Remote Similarity	NPD898	Approved
0.5862	Remote Similarity	NPD896	Approved
0.5859	Remote Similarity	NPD7524	Approved
0.5856	Remote Similarity	NPD8306	Approved
0.5856	Remote Similarity	NPD8305	Approved
0.5842	Remote Similarity	NPD6698	Approved
0.5842	Remote Similarity	NPD46	Approved
0.5823	Remote Similarity	NPD888	Phase 3
0.5823	Remote Similarity	NPD893	Approved
0.5823	Remote Similarity	NPD891	Phase 3
0.5823	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD892	Phase 3
0.5804	Remote Similarity	NPD8087	Discontinued
0.5776	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.575	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.575	Remote Similarity	NPD3730	Approved
0.575	Remote Similarity	NPD3728	Approved
0.5738	Remote Similarity	NPD8293	Discontinued
0.5714	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6123	Approved
0.5691	Remote Similarity	NPD7736	Approved
0.5686	Remote Similarity	NPD7838	Discovery
0.5684	Remote Similarity	NPD7329	Approved
0.5667	Remote Similarity	NPD6370	Approved
0.5641	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7637	Suspended
0.5625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8174	Phase 2
0.5619	Remote Similarity	NPD7991	Discontinued
0.5614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6695	Phase 3
0.5607	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6081	Approved
0.5604	Remote Similarity	NPD5777	Approved
0.5604	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4809	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