NPASS Compound

Structure

NPC475654 OpenBabel07101718322D 46 53 0 0 1 0 0 0 0 0999 V2000 -1.1691 1.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6780 -3.5802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1080 -2.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7621 0.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2320 1.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8382 -1.8237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9818 0.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6923 0.9576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1661 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9239 -3.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4399 0.2304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0540 -3.5938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2920 0.5959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4123 1.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3569 -2.3081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5303 -2.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7013 -0.3340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8017 -1.6075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5239 -0.1666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1585 0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1594 1.8336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8268 1.2881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9552 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8304 0.1758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9318 -2.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2662 0.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3094 0.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 0.8520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8002 -2.0871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6920 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0199 -1.8237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0194 -0.7528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5451 -0.7652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8096 -0.6076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0697 -1.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9475 -0.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0776 -0.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8081 -3.0870 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 0.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7746 2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1259 -0.5116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5643 -1.6433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5580 0.0557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1631 0.8757 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 -3.3708 -1.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 38 1 0 0 0 0 3 42 1 0 0 0 0 4 7 1 0 0 0 0 4 22 2 0 0 0 0 5 8 2 0 0 0 0 5 22 1 0 0 0 0 6 9 2 0 0 0 0 6 23 1 0 0 0 0 7 26 2 0 0 0 0 8 26 1 0 0 0 0 9 30 1 0 0 0 0 10 12 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 38 1 0 0 0 0 13 39 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 23 2 0 0 0 0 16 31 1 0 0 0 0 17 24 2 0 0 0 0 17 32 1 0 0 0 0 18 25 2 0 0 0 0 18 34 1 0 0 0 0 19 27 2 0 0 0 0 19 33 1 0 0 0 0 20 43 1 0 0 0 0 20 44 1 0 0 0 0 21 39 1 0 0 0 0 21 40 2 0 0 0 0 24 27 1 0 0 0 0 25 35 1 0 0 0 0 26 45 1 0 0 0 0 27 28 1 0 0 0 0 28 14 1 6 0 0 0 28 39 1 0 0 0 0 29 15 1 6 0 0 0 29 35 1 0 0 0 0 29 38 1 0 0 0 0 30 31 2 0 0 0 0 30 41 1 0 0 0 0 31 46 1 0 0 0 0 32 33 2 0 0 0 0 32 42 1 0 0 0 0 33 46 1 0 0 0 0 34 36 2 0 0 0 0 34 43 1 0 0 0 0 35 37 2 0 0 0 0 36 37 1 0 0 0 0 36 44 1 0 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.25
Volume:	629.307
LogP:	6.134
LogD:	3.743
LogS:	-7.248
# Rotatable Bonds:	2
TPSA:	89.93
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	5.878
Fsp3:	0.324
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.679
MDCK Permeability:	2.5245002689189278e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.931
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	98.55286407470703%
Volume Distribution (VD):	0.591
Pgp-substrate:	2.1384148597717285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.698
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.333
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.941

ADMET: Excretion

Clearance (CL):	9.173
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.727
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.331
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.473
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.172
Carcinogencity:	0.747
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC475654

Natural Product ID:	NPC475654
*Common Name:**	FIHZBLFUMKZQLN-URLMMPGGSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Isocuricycleatjine
Standard InCHIKey:	FIHZBLFUMKZQLN-URLMMPGGSA-N
Standard InCHI:	InChI=1S/C37H36N2O7/c1-21(40)39-13-11-24-17-32(42-3)33-19-27(24)28(39)14-22-4-7-26(8-5-22)45-37-35-25(18-34-36(37)44-20-43-34)10-12-38(2)29(35)15-23-6-9-30(41)31(16-23)46-33/h4-9,16-19,28-29,41H,10-15,20H2,1-3H3/t28-,29+/m0/s1
SMILES:	CC(=O)N1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C6C(CC7=CC(=C(C=C7)O)O3)N(CCC6=CC8=C5OCO8)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510729
PubChem CID:	44559026
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO14592	Cyclea atjehensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO14592	Cyclea atjehensis	Species	Menispermaceae	Eukaryota	leaves	Thai	n.a.	Database[Title]
NPO14592	Cyclea atjehensis	Species	Menispermaceae	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
ED50	1
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	8870.0	nM	PMID[475665]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6890.0	nM	PMID[475665]
NPT2	Others	Unspecified		Selectivity Index	=	1.3	n.a.	PMID[475665]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4030.0	nM	PMID[475665]
NPT2	Others	Unspecified		Selectivity Index	=	2.2	n.a.	PMID[475665]

☑ 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 NPC475654 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	334
0.1-0.2	1695
0.2-0.3	8131
0.3-0.4	10262
0.4-0.5	6011
0.5-0.6	8941
0.6-0.7	6316
0.7-0.8	824
0.8-0.85	79
0.85-0.9	53
0.9-0.95	47
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC24260
0.9605	High Similarity	NPC473716
0.9605	High Similarity	NPC475597
0.9266	High Similarity	NPC299990
0.9266	High Similarity	NPC328155
0.9266	High Similarity	NPC7715
0.9266	High Similarity	NPC251735
0.9266	High Similarity	NPC290005
0.9266	High Similarity	NPC217748
0.9266	High Similarity	NPC239824
0.9266	High Similarity	NPC290582
0.9266	High Similarity	NPC54654
0.9266	High Similarity	NPC285931
0.9266	High Similarity	NPC185639
0.9266	High Similarity	NPC279228
0.9266	High Similarity	NPC49075
0.9266	High Similarity	NPC258657
0.9266	High Similarity	NPC181796
0.9266	High Similarity	NPC90998
0.9266	High Similarity	NPC182052
0.9266	High Similarity	NPC104196
0.9266	High Similarity	NPC271013
0.9266	High Similarity	NPC15414
0.9266	High Similarity	NPC229373
0.9266	High Similarity	NPC223690
0.9266	High Similarity	NPC73492
0.9266	High Similarity	NPC8836
0.9266	High Similarity	NPC222661
0.9266	High Similarity	NPC42663
0.9266	High Similarity	NPC311973
0.9213	High Similarity	NPC274716
0.9213	High Similarity	NPC254441
0.9213	High Similarity	NPC167116
0.9209	High Similarity	NPC286119
0.9157	High Similarity	NPC30779
0.9111	High Similarity	NPC116465
0.9111	High Similarity	NPC212237
0.9061	High Similarity	NPC22115
0.9061	High Similarity	NPC275680
0.9011	High Similarity	NPC281581
0.9011	High Similarity	NPC48490
0.9011	High Similarity	NPC274661
0.9011	High Similarity	NPC206900
0.9011	High Similarity	NPC82457
0.9011	High Similarity	NPC175890
0.9011	High Similarity	NPC11296
0.8962	High Similarity	NPC60295
0.8962	High Similarity	NPC191132
0.895	High Similarity	NPC302245
0.895	High Similarity	NPC16357
0.895	High Similarity	NPC95426
0.8901	High Similarity	NPC65312
0.8901	High Similarity	NPC139783
0.887	High Similarity	NPC276890
0.887	High Similarity	NPC115284
0.887	High Similarity	NPC227060
0.887	High Similarity	NPC10908
0.887	High Similarity	NPC76682
0.887	High Similarity	NPC317439
0.887	High Similarity	NPC63646
0.887	High Similarity	NPC317145
0.887	High Similarity	NPC198498
0.882	High Similarity	NPC12424
0.882	High Similarity	NPC129518
0.882	High Similarity	NPC251580
0.882	High Similarity	NPC41376
0.8811	High Similarity	NPC478093
0.8763	High Similarity	NPC473589
0.8763	High Similarity	NPC478091
0.8763	High Similarity	NPC478092
0.8763	High Similarity	NPC30182
0.8722	High Similarity	NPC293093
0.8703	High Similarity	NPC82763
0.8663	High Similarity	NPC256124
0.8663	High Similarity	NPC85381
0.8656	High Similarity	NPC41122
0.8656	High Similarity	NPC318805
0.8644	High Similarity	NPC264850
0.8644	High Similarity	NPC256012
0.8644	High Similarity	NPC42549
0.8644	High Similarity	NPC240841
0.8644	High Similarity	NPC268503
0.8644	High Similarity	NPC317272
0.8644	High Similarity	NPC13916
0.8644	High Similarity	NPC250846
0.8626	High Similarity	NPC475479
0.8626	High Similarity	NPC243454
0.8588	High Similarity	NPC232514
0.8588	High Similarity	NPC238530
0.8588	High Similarity	NPC276944
0.8588	High Similarity	NPC24465
0.8579	High Similarity	NPC239584
0.8571	High Similarity	NPC234318
0.8547	High Similarity	NPC83198
0.8547	High Similarity	NPC204908
0.85	High Similarity	NPC82056
0.8432	Intermediate Similarity	NPC116284
0.8407	Intermediate Similarity	NPC190783
0.8407	Intermediate Similarity	NPC232386
0.8407	Intermediate Similarity	NPC152680
0.84	Intermediate Similarity	NPC38964
0.8387	Intermediate Similarity	NPC302275
0.8362	Intermediate Similarity	NPC111485
0.8352	Intermediate Similarity	NPC475215
0.8352	Intermediate Similarity	NPC108434
0.8342	Intermediate Similarity	NPC249996
0.8308	Intermediate Similarity	NPC254581
0.8306	Intermediate Similarity	NPC2314
0.828	Intermediate Similarity	NPC195538
0.827	Intermediate Similarity	NPC320223
0.827	Intermediate Similarity	NPC114364
0.8261	Intermediate Similarity	NPC199465
0.8261	Intermediate Similarity	NPC128560
0.8261	Intermediate Similarity	NPC229166
0.8254	Intermediate Similarity	NPC476576
0.8254	Intermediate Similarity	NPC186546
0.8249	Intermediate Similarity	NPC247639
0.8249	Intermediate Similarity	NPC25084
0.8235	Intermediate Similarity	NPC476202
0.8201	Intermediate Similarity	NPC14507
0.8201	Intermediate Similarity	NPC47077
0.8192	Intermediate Similarity	NPC193949
0.8192	Intermediate Similarity	NPC207757
0.8192	Intermediate Similarity	NPC295691
0.8192	Intermediate Similarity	NPC469817
0.8192	Intermediate Similarity	NPC127674
0.8192	Intermediate Similarity	NPC172765
0.8192	Intermediate Similarity	NPC184026
0.8192	Intermediate Similarity	NPC54379
0.8192	Intermediate Similarity	NPC2413
0.8192	Intermediate Similarity	NPC278799
0.8192	Intermediate Similarity	NPC39701
0.8192	Intermediate Similarity	NPC189266
0.8192	Intermediate Similarity	NPC276588
0.8192	Intermediate Similarity	NPC41178
0.8192	Intermediate Similarity	NPC249797
0.8192	Intermediate Similarity	NPC5238
0.8192	Intermediate Similarity	NPC138487
0.8192	Intermediate Similarity	NPC204828
0.8192	Intermediate Similarity	NPC110416
0.8192	Intermediate Similarity	NPC216459
0.8187	Intermediate Similarity	NPC24228
0.8152	Intermediate Similarity	NPC19520
0.8152	Intermediate Similarity	NPC149090
0.8152	Intermediate Similarity	NPC239775
0.8146	Intermediate Similarity	NPC146288
0.8128	Intermediate Similarity	NPC32154
0.8105	Intermediate Similarity	NPC214116
0.8105	Intermediate Similarity	NPC57036
0.8098	Intermediate Similarity	NPC168753
0.8098	Intermediate Similarity	NPC118274
0.8054	Intermediate Similarity	NPC10871
0.8045	Intermediate Similarity	NPC31311
0.8045	Intermediate Similarity	NPC234392
0.8043	Intermediate Similarity	NPC241055
0.8032	Intermediate Similarity	NPC244554
0.8022	Intermediate Similarity	NPC475393
0.8021	Intermediate Similarity	NPC241704
0.801	Intermediate Similarity	NPC267414
0.8	Intermediate Similarity	NPC75958
0.8	Intermediate Similarity	NPC135772
0.7989	Intermediate Similarity	NPC155442
0.7989	Intermediate Similarity	NPC476574
0.7989	Intermediate Similarity	NPC298979
0.7989	Intermediate Similarity	NPC312918
0.7989	Intermediate Similarity	NPC477561
0.7979	Intermediate Similarity	NPC118633
0.7979	Intermediate Similarity	NPC294790
0.7979	Intermediate Similarity	NPC148693
0.7969	Intermediate Similarity	NPC237579
0.7968	Intermediate Similarity	NPC49353
0.7968	Intermediate Similarity	NPC187678
0.7967	Intermediate Similarity	NPC60186
0.7966	Intermediate Similarity	NPC97221
0.7966	Intermediate Similarity	NPC220858
0.7966	Intermediate Similarity	NPC88249
0.7966	Intermediate Similarity	NPC151895
0.7966	Intermediate Similarity	NPC192768
0.7958	Intermediate Similarity	NPC9867
0.7937	Intermediate Similarity	NPC474507
0.7935	Intermediate Similarity	NPC476432
0.7935	Intermediate Similarity	NPC24264
0.7912	Intermediate Similarity	NPC119649
0.7912	Intermediate Similarity	NPC235143
0.7912	Intermediate Similarity	NPC230956
0.7912	Intermediate Similarity	NPC205255
0.7912	Intermediate Similarity	NPC271388
0.791	Intermediate Similarity	NPC477565
0.791	Intermediate Similarity	NPC103379
0.7895	Intermediate Similarity	NPC257269
0.7895	Intermediate Similarity	NPC32413
0.7895	Intermediate Similarity	NPC230276
0.7895	Intermediate Similarity	NPC474506
0.7892	Intermediate Similarity	NPC12053
0.7892	Intermediate Similarity	NPC145832
0.7892	Intermediate Similarity	NPC306555
0.7892	Intermediate Similarity	NPC474931
0.7892	Intermediate Similarity	NPC81218
0.7892	Intermediate Similarity	NPC247389
0.7892	Intermediate Similarity	NPC158376

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 NPC475654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	713
0.2-0.3	1249
0.3-0.4	2227
0.4-0.5	2520
0.5-0.6	1636
0.6-0.7	501
0.7-0.8	98
0.8-0.85	1
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9266	High Similarity	NPD8054	Approved
0.9266	High Similarity	NPD8053	Approved
0.887	High Similarity	NPD8099	Discontinued
0.887	High Similarity	NPD8252	Approved
0.887	High Similarity	NPD8251	Approved
0.882	High Similarity	NPD8156	Discontinued
0.8135	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD8095	Phase 1
0.7842	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7906	Approved
0.7797	Intermediate Similarity	NPD4584	Approved
0.776	Intermediate Similarity	NPD6788	Approved
0.7668	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6071	Discontinued
0.7617	Intermediate Similarity	NPD7313	Approved
0.7617	Intermediate Similarity	NPD7311	Approved
0.7617	Intermediate Similarity	NPD7312	Approved
0.7617	Intermediate Similarity	NPD7310	Approved
0.7577	Intermediate Similarity	NPD7309	Approved
0.7566	Intermediate Similarity	NPD27	Approved
0.7566	Intermediate Similarity	NPD2489	Approved
0.7559	Intermediate Similarity	NPD6997	Phase 2
0.7553	Intermediate Similarity	NPD3051	Approved
0.7541	Intermediate Similarity	NPD4772	Phase 2
0.7541	Intermediate Similarity	NPD4773	Phase 2
0.7537	Intermediate Similarity	NPD5005	Approved
0.7537	Intermediate Similarity	NPD5006	Approved
0.7527	Intermediate Similarity	NPD7833	Phase 2
0.7527	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7831	Phase 2
0.7526	Intermediate Similarity	NPD4578	Approved
0.7526	Intermediate Similarity	NPD7281	Phase 3
0.7526	Intermediate Similarity	NPD4577	Approved
0.7526	Intermediate Similarity	NPD7280	Phase 3
0.7524	Intermediate Similarity	NPD7047	Phase 3
0.7522	Intermediate Similarity	NPD8153	Approved
0.7522	Intermediate Similarity	NPD8152	Approved
0.7513	Intermediate Similarity	NPD2970	Approved
0.7513	Intermediate Similarity	NPD2969	Approved
0.75	Intermediate Similarity	NPD4663	Approved
0.7475	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7549	Discontinued
0.7464	Intermediate Similarity	NPD7827	Phase 1
0.7459	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2560	Approved
0.7419	Intermediate Similarity	NPD2563	Approved
0.7405	Intermediate Similarity	NPD7298	Approved
0.7382	Intermediate Similarity	NPD2898	Approved
0.7382	Intermediate Similarity	NPD4481	Phase 3
0.7358	Intermediate Similarity	NPD5313	Approved
0.7358	Intermediate Similarity	NPD5312	Approved
0.734	Intermediate Similarity	NPD4420	Approved
0.7337	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2494	Approved
0.7317	Intermediate Similarity	NPD3450	Approved
0.7317	Intermediate Similarity	NPD3452	Approved
0.7317	Intermediate Similarity	NPD2493	Approved
0.731	Intermediate Similarity	NPD6851	Approved
0.731	Intermediate Similarity	NPD6853	Approved
0.7308	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7447	Phase 1
0.73	Intermediate Similarity	NPD2488	Approved
0.73	Intermediate Similarity	NPD2490	Approved
0.7282	Intermediate Similarity	NPD6297	Approved
0.7277	Intermediate Similarity	NPD4166	Phase 2
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5677	Discontinued
0.724	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6107	Approved
0.7212	Intermediate Similarity	NPD4583	Approved
0.7212	Intermediate Similarity	NPD4582	Approved
0.7208	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4010	Discontinued
0.7181	Intermediate Similarity	NPD2977	Approved
0.7181	Intermediate Similarity	NPD2978	Approved
0.7175	Intermediate Similarity	NPD6723	Discontinued
0.7163	Intermediate Similarity	NPD4002	Approved
0.7163	Intermediate Similarity	NPD4004	Approved
0.7158	Intermediate Similarity	NPD7213	Phase 3
0.7158	Intermediate Similarity	NPD7212	Phase 2
0.7157	Intermediate Similarity	NPD5582	Discontinued
0.7143	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3641	Approved
0.7135	Intermediate Similarity	NPD3639	Approved
0.7135	Intermediate Similarity	NPD3640	Phase 3
0.7129	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2973	Approved
0.7122	Intermediate Similarity	NPD2975	Approved
0.7122	Intermediate Similarity	NPD2974	Approved
0.712	Intermediate Similarity	NPD1424	Approved
0.7095	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6042	Phase 2
0.7092	Intermediate Similarity	NPD42	Phase 2
0.7068	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4055	Discovery
0.7065	Intermediate Similarity	NPD2420	Approved
0.7065	Intermediate Similarity	NPD2421	Approved
0.7059	Intermediate Similarity	NPD7224	Discontinued
0.7059	Intermediate Similarity	NPD7223	Discontinued
0.7056	Intermediate Similarity	NPD3885	Approved
0.7049	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6030	Approved
0.7043	Intermediate Similarity	NPD6031	Approved
0.7041	Intermediate Similarity	NPD7228	Approved
0.703	Intermediate Similarity	NPD6842	Approved
0.703	Intermediate Similarity	NPD6843	Phase 3
0.703	Intermediate Similarity	NPD6841	Approved
0.703	Intermediate Similarity	NPD7291	Discontinued
0.7021	Intermediate Similarity	NPD4675	Approved
0.7021	Intermediate Similarity	NPD4678	Approved
0.7019	Intermediate Similarity	NPD5457	Discontinued
0.7019	Intermediate Similarity	NPD4580	Approved
0.7011	Intermediate Similarity	NPD7124	Phase 2
0.7	Intermediate Similarity	NPD5773	Approved
0.7	Intermediate Similarity	NPD2968	Approved
0.7	Intermediate Similarity	NPD2971	Approved
0.7	Intermediate Similarity	NPD5772	Approved
0.6995	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7584	Approved
0.6979	Remote Similarity	NPD5604	Discontinued
0.6973	Remote Similarity	NPD5297	Approved
0.6968	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4017	Approved
0.6967	Remote Similarity	NPD4040	Phase 1
0.6959	Remote Similarity	NPD7802	Discontinued
0.6959	Remote Similarity	NPD7199	Phase 2
0.6957	Remote Similarity	NPD5241	Discontinued
0.6954	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3384	Approved
0.6947	Remote Similarity	NPD3383	Approved
0.6947	Remote Similarity	NPD3382	Approved
0.693	Remote Similarity	NPD7048	Phase 3
0.6927	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3845	Phase 1
0.6915	Remote Similarity	NPD4210	Discontinued
0.6902	Remote Similarity	NPD7466	Approved
0.6901	Remote Similarity	NPD7263	Phase 2
0.6895	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7110	Phase 1
0.6889	Remote Similarity	NPD2492	Phase 1
0.6888	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6618	Phase 2
0.6878	Remote Similarity	NPD4005	Discontinued
0.6875	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6625	Approved
0.6869	Remote Similarity	NPD7585	Approved
0.6869	Remote Similarity	NPD7701	Phase 2
0.6869	Remote Similarity	NPD7177	Discontinued
0.6856	Remote Similarity	NPD6234	Discontinued
0.6856	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7296	Approved
0.6832	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6666	Approved
0.6828	Remote Similarity	NPD6667	Approved
0.6823	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7583	Approved
0.6821	Remote Similarity	NPD2904	Discontinued
0.6821	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4474	Approved
0.6816	Remote Similarity	NPD4475	Approved
0.6816	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6748	Discontinued
0.6806	Remote Similarity	NPD6072	Discontinued
0.6804	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7907	Approved
0.68	Remote Similarity	NPD8059	Phase 3
0.68	Remote Similarity	NPD7074	Phase 3
0.68	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7598	Phase 2
0.6789	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3349	Phase 2
0.678	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6493	Phase 3
0.6776	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2122	Discontinued
0.6772	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7007	Discovery
0.676	Remote Similarity	NPD5718	Phase 2
0.6758	Remote Similarity	NPD2200	Suspended
0.6757	Remote Similarity	NPD5177	Phase 3
0.6757	Remote Similarity	NPD4237	Approved
0.6757	Remote Similarity	NPD4236	Phase 3
0.6755	Remote Similarity	NPD4123	Phase 3
0.675	Remote Similarity	NPD4873	Discontinued
0.675	Remote Similarity	NPD7054	Approved
0.6742	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1529	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