NPASS Compound

Structure

NPC309211 OpenBabel07101718292D 42 43 0 0 1 0 0 0 0 0999 V2000 -20.9813 -4.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.1722 -5.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.2587 -5.0936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.1542 -4.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.2406 -3.6923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1361 -2.6978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.2225 -2.2910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.1180 -1.2965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.2045 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5388 2.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0388 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.0999 0.1047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5388 2.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0388 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.1864 0.5115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0388 3.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.3774 -0.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0388 3.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4638 0.3304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5388 2.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8752 -0.3506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1321 0.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 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 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 0.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.6548 -0.2574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0388 2.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.7413 0.1494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.5388 1.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7593 -1.2519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0388 2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 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 -11.5334 1.1275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 29 1 0 0 0 0 28 30 2 0 0 0 0 29 2 1 1 0 0 0 29 41 1 0 0 0 0 30 36 1 0 0 0 0 31 37 1 6 0 0 0 32 38 1 6 0 0 0 33 39 1 1 0 0 0 34 32 1 6 0 0 0 34 42 1 0 0 0 0 35 33 1 1 0 0 0 35 42 1 0 0 0 0 36 40 2 0 0 0 0 36 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.47
Volume:	658.931
LogP:	8.402
LogD:	4.717
LogS:	-4.324
# Rotatable Bonds:	26
TPSA:	103.29
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.063
Synthetic Accessibility Score:	4.455
Fsp3:	0.833
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.221
MDCK Permeability:	2.6530307877692394e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.677
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	100.38941192626953%
Volume Distribution (VD):	1.26
Pgp-substrate:	1.2726678848266602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.631
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	4.15
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.413
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.772
Skin Sensitization:	0.976
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.195

Download Data

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

Natural Product: NPC309211

Natural Product ID:	NPC309211
*Common Name:**	Calamistrin E
IUPAC Name:	(2S)-4-[(3R,13R)-3,13-dihydroxy-13-[(2R,5R)-5-[(Z,1R)-1-hydroxytetradec-4-enyl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Calamistrin E
Standard InCHIKey:	UNXIMIFMCNSOAC-QBXDJIRYSA-N
Standard InCHI:	InChI=1S/C36H64O6/c1-3-4-5-6-7-8-9-10-13-16-19-22-32(38)34-26-27-35(42-34)33(39)23-20-17-14-11-12-15-18-21-31(37)25-24-30-28-29(2)41-36(30)40/h13,16,28-29,31-35,37-39H,3-12,14-15,17-27H2,1-2H3/b16-13-/t29-,31+,32+,33+,34+,35+/m0/s1
SMILES:	CCCCCCCCC/C=CCC[C@H]([C@H]1CC[C@H]([C@@H](CCCCCCCCC[C@H](CCC2=C[C@H](C)OC2=O)O)O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451654
PubChem CID:	11801608
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075755]
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000019]
NPO210	Uvaria calamistrata	Species	Annonaceae	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
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	0.0273	ug.mL-1	PMID[520084]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.375	ug.mL-1	PMID[520084]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.00397	ug.mL-1	PMID[520084]

☑ 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 NPC309211 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	175
0.1-0.2	1350
0.2-0.3	5620
0.3-0.4	12978
0.4-0.5	12313
0.5-0.6	6810
0.6-0.7	2731
0.7-0.8	519
0.8-0.85	45
0.85-0.9	39
0.9-0.95	109
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC477018
0.9875	High Similarity	NPC100921
0.9753	High Similarity	NPC477010
0.9634	High Similarity	NPC473649
0.9634	High Similarity	NPC159750
0.9634	High Similarity	NPC470401
0.9634	High Similarity	NPC154097
0.963	High Similarity	NPC322529
0.9625	High Similarity	NPC253801
0.9518	High Similarity	NPC89001
0.9506	High Similarity	NPC156804
0.95	High Similarity	NPC11332
0.95	High Similarity	NPC473529
0.95	High Similarity	NPC65930
0.95	High Similarity	NPC473712
0.95	High Similarity	NPC73310
0.95	High Similarity	NPC131002
0.95	High Similarity	NPC329829
0.95	High Similarity	NPC180363
0.95	High Similarity	NPC473780
0.95	High Similarity	NPC475159
0.95	High Similarity	NPC145914
0.95	High Similarity	NPC94875
0.9405	High Similarity	NPC477017
0.9405	High Similarity	NPC477016
0.9405	High Similarity	NPC477011
0.939	High Similarity	NPC470400
0.939	High Similarity	NPC77871
0.939	High Similarity	NPC329838
0.939	High Similarity	NPC475268
0.939	High Similarity	NPC39167
0.939	High Similarity	NPC473156
0.939	High Similarity	NPC235809
0.939	High Similarity	NPC25764
0.939	High Similarity	NPC202055
0.939	High Similarity	NPC120398
0.939	High Similarity	NPC9678
0.939	High Similarity	NPC329615
0.939	High Similarity	NPC471567
0.939	High Similarity	NPC319036
0.939	High Similarity	NPC39279
0.939	High Similarity	NPC292809
0.939	High Similarity	NPC473671
0.9383	High Similarity	NPC144415
0.9277	High Similarity	NPC114694
0.9277	High Similarity	NPC293136
0.9277	High Similarity	NPC62118
0.9277	High Similarity	NPC219652
0.9277	High Similarity	NPC132940
0.9277	High Similarity	NPC282815
0.9277	High Similarity	NPC171174
0.9277	High Similarity	NPC25703
0.9277	High Similarity	NPC69082
0.9277	High Similarity	NPC142117
0.9277	High Similarity	NPC475581
0.9277	High Similarity	NPC107717
0.9277	High Similarity	NPC473840
0.9277	High Similarity	NPC231096
0.9277	High Similarity	NPC232555
0.9277	High Similarity	NPC112685
0.9277	High Similarity	NPC240695
0.9277	High Similarity	NPC279267
0.9277	High Similarity	NPC241360
0.9268	High Similarity	NPC163093
0.9176	High Similarity	NPC280612
0.9167	High Similarity	NPC258068
0.9167	High Similarity	NPC477012
0.9167	High Similarity	NPC476583
0.9167	High Similarity	NPC473995
0.9167	High Similarity	NPC20533
0.9157	High Similarity	NPC66346
0.9157	High Similarity	NPC286338
0.9157	High Similarity	NPC223871
0.9157	High Similarity	NPC473478
0.9157	High Similarity	NPC473669
0.9157	High Similarity	NPC231009
0.9157	High Similarity	NPC473651
0.9157	High Similarity	NPC107986
0.9157	High Similarity	NPC477013
0.9157	High Similarity	NPC110710
0.9157	High Similarity	NPC103284
0.9157	High Similarity	NPC1083
0.9157	High Similarity	NPC82795
0.9157	High Similarity	NPC283085
0.9157	High Similarity	NPC477014
0.9157	High Similarity	NPC132496
0.9059	High Similarity	NPC40376
0.9059	High Similarity	NPC242364
0.9059	High Similarity	NPC280621
0.9059	High Similarity	NPC320458
0.9059	High Similarity	NPC48338
0.9059	High Similarity	NPC234077
0.9059	High Similarity	NPC261952
0.9059	High Similarity	NPC100454
0.9059	High Similarity	NPC169511
0.9059	High Similarity	NPC151403
0.9059	High Similarity	NPC287164
0.9059	High Similarity	NPC172821
0.9059	High Similarity	NPC61257
0.9059	High Similarity	NPC473905
0.9059	High Similarity	NPC274446
0.9059	High Similarity	NPC191929
0.9059	High Similarity	NPC81045
0.9059	High Similarity	NPC21208
0.9059	High Similarity	NPC320569
0.9059	High Similarity	NPC171135
0.9059	High Similarity	NPC39754
0.9059	High Similarity	NPC133730
0.9059	High Similarity	NPC233551
0.9059	High Similarity	NPC20339
0.9048	High Similarity	NPC134865
0.9048	High Similarity	NPC103523
0.9048	High Similarity	NPC210218
0.9048	High Similarity	NPC473687
0.9048	High Similarity	NPC204686
0.9048	High Similarity	NPC134885
0.9048	High Similarity	NPC134807
0.9048	High Similarity	NPC308412
0.9048	High Similarity	NPC219498
0.9048	High Similarity	NPC477015
0.8953	High Similarity	NPC40066
0.8953	High Similarity	NPC93794
0.8953	High Similarity	NPC473504
0.8953	High Similarity	NPC81778
0.8953	High Similarity	NPC42598
0.8953	High Similarity	NPC318963
0.8953	High Similarity	NPC91067
0.8953	High Similarity	NPC20621
0.8941	High Similarity	NPC178215
0.8864	High Similarity	NPC11456
0.8851	High Similarity	NPC239517
0.8851	High Similarity	NPC473904
0.8824	High Similarity	NPC47937
0.8736	High Similarity	NPC14901
0.8736	High Similarity	NPC139418
0.8736	High Similarity	NPC130359
0.8706	High Similarity	NPC182383
0.8652	High Similarity	NPC473520
0.8652	High Similarity	NPC475173
0.8652	High Similarity	NPC473561
0.8652	High Similarity	NPC473663
0.8652	High Similarity	NPC473723
0.8539	High Similarity	NPC473707
0.8427	Intermediate Similarity	NPC474761
0.8427	Intermediate Similarity	NPC476004
0.8333	Intermediate Similarity	NPC30515
0.8315	Intermediate Similarity	NPC295312
0.8276	Intermediate Similarity	NPC21469
0.8242	Intermediate Similarity	NPC81419
0.8242	Intermediate Similarity	NPC179746
0.8222	Intermediate Similarity	NPC473619
0.8222	Intermediate Similarity	NPC51004
0.8182	Intermediate Similarity	NPC164393
0.8161	Intermediate Similarity	NPC474251
0.8148	Intermediate Similarity	NPC474705
0.8132	Intermediate Similarity	NPC12172
0.8132	Intermediate Similarity	NPC473321
0.8132	Intermediate Similarity	NPC208886
0.8132	Intermediate Similarity	NPC184463
0.8111	Intermediate Similarity	NPC307411
0.8111	Intermediate Similarity	NPC474032
0.809	Intermediate Similarity	NPC248602
0.8068	Intermediate Similarity	NPC137033
0.8065	Intermediate Similarity	NPC36954
0.8046	Intermediate Similarity	NPC11620
0.8043	Intermediate Similarity	NPC476300
0.8043	Intermediate Similarity	NPC295204
0.8043	Intermediate Similarity	NPC162205
0.8043	Intermediate Similarity	NPC288240
0.8043	Intermediate Similarity	NPC475912
0.8043	Intermediate Similarity	NPC273579
0.8025	Intermediate Similarity	NPC84038
0.8022	Intermediate Similarity	NPC473448
0.8	Intermediate Similarity	NPC153805
0.8	Intermediate Similarity	NPC473326
0.8	Intermediate Similarity	NPC202672
0.8	Intermediate Similarity	NPC227379
0.8	Intermediate Similarity	NPC474471
0.7978	Intermediate Similarity	NPC284902
0.7976	Intermediate Similarity	NPC475711
0.7957	Intermediate Similarity	NPC81386
0.7957	Intermediate Similarity	NPC474035
0.7955	Intermediate Similarity	NPC474780
0.7889	Intermediate Similarity	NPC160138
0.7875	Intermediate Similarity	NPC218477
0.7872	Intermediate Similarity	NPC270013
0.7872	Intermediate Similarity	NPC14961
0.7865	Intermediate Similarity	NPC329749
0.7865	Intermediate Similarity	NPC475206
0.7857	Intermediate Similarity	NPC110989
0.7849	Intermediate Similarity	NPC212486
0.7816	Intermediate Similarity	NPC297440
0.7802	Intermediate Similarity	NPC473715
0.7802	Intermediate Similarity	NPC58219
0.7802	Intermediate Similarity	NPC281516
0.7802	Intermediate Similarity	NPC177629
0.7791	Intermediate Similarity	NPC470149
0.7791	Intermediate Similarity	NPC470148
0.7789	Intermediate Similarity	NPC476315
0.7789	Intermediate Similarity	NPC477921

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 NPC309211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	2068
0.2-0.3	3927
0.3-0.4	2086
0.4-0.5	619
0.5-0.6	244
0.6-0.7	51
0.7-0.8	4
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
0.7634	Intermediate Similarity	NPD6698	Approved
0.7634	Intermediate Similarity	NPD46	Approved
0.7553	Intermediate Similarity	NPD7983	Approved
0.7447	Intermediate Similarity	NPD7838	Discovery
0.7282	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6686	Approved
0.697	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3197	Phase 1
0.6931	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4250	Approved
0.6771	Remote Similarity	NPD4251	Approved
0.6759	Remote Similarity	NPD6371	Approved
0.6735	Remote Similarity	NPD5785	Approved
0.6702	Remote Similarity	NPD7154	Phase 3
0.6702	Remote Similarity	NPD5362	Discontinued
0.6697	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4249	Approved
0.66	Remote Similarity	NPD5778	Approved
0.66	Remote Similarity	NPD5779	Approved
0.6596	Remote Similarity	NPD6435	Approved
0.6569	Remote Similarity	NPD7839	Suspended
0.6562	Remote Similarity	NPD5363	Approved
0.6495	Remote Similarity	NPD5786	Approved
0.6486	Remote Similarity	NPD6053	Discontinued
0.6476	Remote Similarity	NPD5344	Discontinued
0.6466	Remote Similarity	NPD8513	Phase 3
0.6466	Remote Similarity	NPD8517	Approved
0.6466	Remote Similarity	NPD8516	Approved
0.6466	Remote Similarity	NPD8515	Approved
0.6442	Remote Similarity	NPD4225	Approved
0.6442	Remote Similarity	NPD7638	Approved
0.6421	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4756	Discovery
0.6392	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7507	Approved
0.6386	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5368	Approved
0.6383	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7639	Approved
0.6381	Remote Similarity	NPD7640	Approved
0.6374	Remote Similarity	NPD8039	Approved
0.6356	Remote Similarity	NPD7830	Approved
0.6356	Remote Similarity	NPD7829	Approved
0.6354	Remote Similarity	NPD6110	Phase 1
0.6344	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.63	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD3196	Approved
0.625	Remote Similarity	NPD3194	Approved
0.625	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD4266	Approved
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD5209	Approved
0.623	Remote Similarity	NPD7319	Approved
0.6224	Remote Similarity	NPD1694	Approved
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4252	Approved
0.6198	Remote Similarity	NPD8074	Phase 3
0.6186	Remote Similarity	NPD5332	Approved
0.6186	Remote Similarity	NPD5331	Approved
0.617	Remote Similarity	NPD4271	Approved
0.617	Remote Similarity	NPD4268	Approved
0.6146	Remote Similarity	NPD4790	Discontinued
0.6146	Remote Similarity	NPD5369	Approved
0.6145	Remote Similarity	NPD6109	Phase 1
0.6142	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4632	Approved
0.6139	Remote Similarity	NPD6101	Approved
0.6139	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3172	Approved
0.6122	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7115	Discovery
0.6092	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7642	Approved
0.6075	Remote Similarity	NPD6648	Approved
0.6068	Remote Similarity	NPD7641	Discontinued
0.6058	Remote Similarity	NPD5282	Discontinued
0.6053	Remote Similarity	NPD8297	Approved
0.605	Remote Similarity	NPD8444	Approved
0.6049	Remote Similarity	NPD3728	Approved
0.6049	Remote Similarity	NPD3730	Approved
0.6042	Remote Similarity	NPD4821	Approved
0.6042	Remote Similarity	NPD4820	Approved
0.6042	Remote Similarity	NPD4819	Approved
0.6042	Remote Similarity	NPD4822	Approved
0.6033	Remote Similarity	NPD7492	Approved
0.6023	Remote Similarity	NPD7331	Phase 2
0.6019	Remote Similarity	NPD6411	Approved
0.6016	Remote Similarity	NPD7736	Approved
0.5984	Remote Similarity	NPD6616	Approved
0.5966	Remote Similarity	NPD6319	Approved
0.5966	Remote Similarity	NPD6054	Approved
0.5935	Remote Similarity	NPD7078	Approved
0.5893	Remote Similarity	NPD6412	Phase 2
0.5877	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD6927	Phase 3
0.5875	Remote Similarity	NPD29	Approved
0.5875	Remote Similarity	NPD28	Approved
0.5873	Remote Similarity	NPD7260	Phase 2
0.5868	Remote Similarity	NPD6370	Approved
0.5865	Remote Similarity	NPD7637	Suspended
0.5862	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8451	Approved
0.5847	Remote Similarity	NPD6009	Approved
0.5843	Remote Similarity	NPD3704	Approved
0.5843	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6422	Discontinued
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD6881	Approved
0.5841	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8377	Approved
0.5833	Remote Similarity	NPD8294	Approved
0.5826	Remote Similarity	NPD8130	Phase 1
0.5826	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5370	Suspended
0.582	Remote Similarity	NPD7604	Phase 2
0.5818	Remote Similarity	NPD7632	Discontinued
0.5806	Remote Similarity	NPD8293	Discontinued
0.5806	Remote Similarity	NPD8448	Approved
0.5798	Remote Similarity	NPD7328	Approved
0.5798	Remote Similarity	NPD7327	Approved
0.5794	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD5983	Phase 2
0.5785	Remote Similarity	NPD8379	Approved
0.5785	Remote Similarity	NPD6015	Approved
0.5785	Remote Similarity	NPD6016	Approved
0.5785	Remote Similarity	NPD8296	Approved
0.5785	Remote Similarity	NPD8380	Approved
0.5785	Remote Similarity	NPD8335	Approved
0.5785	Remote Similarity	NPD8033	Approved
0.5785	Remote Similarity	NPD8378	Approved
0.5766	Remote Similarity	NPD6647	Phase 2
0.5755	Remote Similarity	NPD7748	Approved
0.5752	Remote Similarity	NPD5697	Approved
0.575	Remote Similarity	NPD7516	Approved
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD6421	Discontinued
0.5739	Remote Similarity	NPD7102	Approved
0.5738	Remote Similarity	NPD5988	Approved
0.5726	Remote Similarity	NPD6336	Discontinued
0.5726	Remote Similarity	NPD8273	Phase 1
0.5714	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6079	Approved
0.5714	Remote Similarity	NPD7500	Approved
0.5703	Remote Similarity	NPD6845	Suspended
0.5702	Remote Similarity	NPD6059	Approved
0.5702	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD6011	Approved
0.5691	Remote Similarity	NPD8328	Phase 3
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6617	Approved
0.569	Remote Similarity	NPD6649	Approved
0.569	Remote Similarity	NPD2204	Approved
0.5669	Remote Similarity	NPD8391	Approved
0.5669	Remote Similarity	NPD8392	Approved
0.5669	Remote Similarity	NPD8390	Approved
0.5664	Remote Similarity	NPD6402	Approved
0.5664	Remote Similarity	NPD6675	Approved
0.5664	Remote Similarity	NPD5739	Approved
0.5664	Remote Similarity	NPD6008	Approved
0.5664	Remote Similarity	NPD7128	Approved
0.5656	Remote Similarity	NPD7503	Approved
0.5652	Remote Similarity	NPD6012	Approved
0.5652	Remote Similarity	NPD6013	Approved
0.5652	Remote Similarity	NPD6014	Approved
0.5645	Remote Similarity	NPD8340	Approved
0.5645	Remote Similarity	NPD8342	Approved
0.5645	Remote Similarity	NPD8299	Approved
0.5645	Remote Similarity	NPD8341	Approved
0.5641	Remote Similarity	NPD6882	Approved
0.5625	Remote Similarity	NPD3173	Approved
0.5618	Remote Similarity	NPD7909	Approved
0.5614	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8080	Discontinued
0.5603	Remote Similarity	NPD2067	Discontinued
0.56	Remote Similarity	NPD4800	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