NPASS Compound

Structure

CID117185 OpenBabel06191715472D 38 41 0 0 1 0 0 0 0 0999 V2000 -3.3014 3.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1563 3.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2568 0.0031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4552 -0.9279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5058 0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0244 -2.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6513 2.8575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8259 2.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3006 0.9513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3252 -1.7382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6490 0.9527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8251 -0.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4764 2.3808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4761 1.4280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1254 1.4275 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6493 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8256 1.4285 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2562 -1.5397 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6878 -1.0312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6505 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8254 -0.4762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1257 2.3804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3011 2.8570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5498 -0.6342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6507 0.9518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8259 -1.4281 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9804 0.9336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5047 -0.4928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8935 -2.2467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9815 -0.1257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5055 -0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9718 2.8684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9124 0.0728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1189 -2.0654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 27 1 0 0 0 0 14 22 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 29 1 6 0 0 0 17 24 1 0 0 0 0 17 31 1 6 0 0 0 18 23 1 0 0 0 0 18 32 1 1 0 0 0 19 27 1 1 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 33 1 0 0 0 0 21 30 1 0 0 0 0 21 34 2 0 0 0 0 22 29 1 0 0 0 0 22 35 2 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 36 2 0 0 0 0 26 37 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 1 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.32
Volume:	552.986
LogP:	1.993
LogD:	0.887
LogS:	-3.615
# Rotatable Bonds:	5
TPSA:	152.36
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	5.466
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
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:	-5.039
MDCK Permeability:	8.364188943232875e-06
Pgp-inhibitor:	0.554
Pgp-substrate:	0.114
Human Intestinal Absorption (HIA):	0.154
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.816

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.669
Plasma Protein Binding (PPB):	55.60497283935547%
Volume Distribution (VD):	0.41
Pgp-substrate:	24.69172477722168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.411
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	3.154
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.301
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.098
Carcinogencity:	0.636
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.468

Download Data

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

Natural Product: NPC117185

Natural Product ID:	NPC117185
*Common Name:**	Cucurbitacin G
IUPAC Name:	(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-17-[(2R)-2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl]-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:	Cucurbitacin G
Standard InCHIKey:	ABNDMUIXCBUBLO-REQJDAJISA-N
Standard InCHI:	InChI=1S/C30H46O8/c1-25(2)15-9-10-19-27(5)13-18(32)23(30(8,38)21(34)12-20(33)26(3,4)37)28(27,6)14-22(35)29(19,7)16(15)11-17(31)24(25)36/h9,16-20,23,31-33,37-38H,10-14H2,1-8H3/t16-,17+,18-,19+,20?,23+,27+,28-,29+,30+/m1/s1
SMILES:	CC1(C)C2=CC[C@H]3[C@]4(C)C[C@H]([C@@H]([C@@]4(C)CC(=O)[C@@]3(C)[C@@H]2C[C@@H](C1=O)O)[C@](C)(C(=O)CC(C(C)(C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551160
PubChem CID:	441818
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO13846	Crinodendron hookerianum	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14700	Citrullus sp.	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8800	Cucumis angolensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13846	Crinodendron hookerianum	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13846	Crinodendron hookerianum	Species	Elaeocarpaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	1280.0	nM	PMID[479918]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1370.0	nM	PMID[479918]

☑ 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 NPC117185 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	205
0.1-0.2	1390
0.2-0.3	5384
0.3-0.4	11005
0.4-0.5	10282
0.5-0.6	6089
0.6-0.7	6087
0.7-0.8	2060
0.8-0.85	138
0.85-0.9	50
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9368	High Similarity	NPC49371
0.93	High Similarity	NPC43285
0.93	High Similarity	NPC58370
0.9192	High Similarity	NPC191892
0.9118	High Similarity	NPC470257
0.9109	High Similarity	NPC165873
0.8846	High Similarity	NPC235077
0.8824	High Similarity	NPC196528
0.8774	High Similarity	NPC108721
0.8774	High Similarity	NPC73300
0.8738	High Similarity	NPC83744
0.87	High Similarity	NPC474720
0.87	High Similarity	NPC15390
0.8687	High Similarity	NPC18509
0.8679	High Similarity	NPC280782
0.8673	High Similarity	NPC472485
0.8654	High Similarity	NPC329417
0.8641	High Similarity	NPC476027
0.8641	High Similarity	NPC85829
0.8641	High Similarity	NPC150531
0.8641	High Similarity	NPC97202
0.8641	High Similarity	NPC214264
0.8641	High Similarity	NPC319077
0.8641	High Similarity	NPC166607
0.8641	High Similarity	NPC260268
0.8641	High Similarity	NPC171137
0.8641	High Similarity	NPC49958
0.8641	High Similarity	NPC302607
0.8641	High Similarity	NPC48733
0.8641	High Similarity	NPC50692
0.8641	High Similarity	NPC152695
0.8641	High Similarity	NPC202167
0.8641	High Similarity	NPC296945
0.8632	High Similarity	NPC470417
0.8571	High Similarity	NPC11710
0.8558	High Similarity	NPC220229
0.8558	High Similarity	NPC477916
0.8558	High Similarity	NPC475060
0.8544	High Similarity	NPC209502
0.8544	High Similarity	NPC204833
0.8544	High Similarity	NPC160843
0.8529	High Similarity	NPC473928
0.8526	High Similarity	NPC90652
0.8515	High Similarity	NPC110149
0.8515	High Similarity	NPC144956
0.85	High Similarity	NPC190554
0.8476	Intermediate Similarity	NPC217201
0.8462	Intermediate Similarity	NPC149047
0.8454	Intermediate Similarity	NPC171441
0.8447	Intermediate Similarity	NPC311612
0.8396	Intermediate Similarity	NPC214644
0.8384	Intermediate Similarity	NPC111015
0.8364	Intermediate Similarity	NPC239273
0.8351	Intermediate Similarity	NPC477943
0.8351	Intermediate Similarity	NPC76879
0.8351	Intermediate Similarity	NPC326627
0.8351	Intermediate Similarity	NPC310010
0.835	Intermediate Similarity	NPC477915
0.835	Intermediate Similarity	NPC87351
0.8333	Intermediate Similarity	NPC218383
0.8333	Intermediate Similarity	NPC207251
0.8333	Intermediate Similarity	NPC154072
0.8333	Intermediate Similarity	NPC83709
0.8317	Intermediate Similarity	NPC170978
0.8316	Intermediate Similarity	NPC474218
0.8302	Intermediate Similarity	NPC65941
0.8286	Intermediate Similarity	NPC257353
0.8283	Intermediate Similarity	NPC474807
0.8283	Intermediate Similarity	NPC233118
0.8269	Intermediate Similarity	NPC140723
0.8257	Intermediate Similarity	NPC52634
0.8257	Intermediate Similarity	NPC962
0.8257	Intermediate Similarity	NPC317210
0.8257	Intermediate Similarity	NPC250109
0.8247	Intermediate Similarity	NPC328313
0.8235	Intermediate Similarity	NPC191565
0.8235	Intermediate Similarity	NPC147954
0.8224	Intermediate Similarity	NPC304495
0.8214	Intermediate Similarity	NPC319570
0.8211	Intermediate Similarity	NPC82902
0.82	Intermediate Similarity	NPC196485
0.82	Intermediate Similarity	NPC174051
0.82	Intermediate Similarity	NPC245972
0.82	Intermediate Similarity	NPC67831
0.819	Intermediate Similarity	NPC75531
0.819	Intermediate Similarity	NPC149124
0.819	Intermediate Similarity	NPC137657
0.819	Intermediate Similarity	NPC471293
0.819	Intermediate Similarity	NPC29705
0.819	Intermediate Similarity	NPC477812
0.8182	Intermediate Similarity	NPC154101
0.8182	Intermediate Similarity	NPC326542
0.8182	Intermediate Similarity	NPC473898
0.8182	Intermediate Similarity	NPC168027
0.8182	Intermediate Similarity	NPC185936
0.8174	Intermediate Similarity	NPC473255
0.8173	Intermediate Similarity	NPC271980
0.8173	Intermediate Similarity	NPC193934
0.8163	Intermediate Similarity	NPC474245
0.8163	Intermediate Similarity	NPC32830
0.8158	Intermediate Similarity	NPC222688
0.8155	Intermediate Similarity	NPC167974
0.8148	Intermediate Similarity	NPC76084
0.8144	Intermediate Similarity	NPC472482
0.8144	Intermediate Similarity	NPC317590
0.8144	Intermediate Similarity	NPC472481
0.8144	Intermediate Similarity	NPC472484
0.8142	Intermediate Similarity	NPC109973
0.8137	Intermediate Similarity	NPC477268
0.8137	Intermediate Similarity	NPC477267
0.8137	Intermediate Similarity	NPC472689
0.8137	Intermediate Similarity	NPC472690
0.8131	Intermediate Similarity	NPC94529
0.8131	Intermediate Similarity	NPC9013
0.8119	Intermediate Similarity	NPC472824
0.8119	Intermediate Similarity	NPC263347
0.8119	Intermediate Similarity	NPC473170
0.8113	Intermediate Similarity	NPC475494
0.8108	Intermediate Similarity	NPC148458
0.8108	Intermediate Similarity	NPC266728
0.8108	Intermediate Similarity	NPC49492
0.81	Intermediate Similarity	NPC206810
0.81	Intermediate Similarity	NPC470376
0.81	Intermediate Similarity	NPC470375
0.8095	Intermediate Similarity	NPC111323
0.8095	Intermediate Similarity	NPC247957
0.8095	Intermediate Similarity	NPC249187
0.8091	Intermediate Similarity	NPC202889
0.8091	Intermediate Similarity	NPC194100
0.8087	Intermediate Similarity	NPC1980
0.8087	Intermediate Similarity	NPC238005
0.8087	Intermediate Similarity	NPC141196
0.8081	Intermediate Similarity	NPC289213
0.8081	Intermediate Similarity	NPC136801
0.8081	Intermediate Similarity	NPC320026
0.8081	Intermediate Similarity	NPC46758
0.8073	Intermediate Similarity	NPC472003
0.8073	Intermediate Similarity	NPC207689
0.807	Intermediate Similarity	NPC470921
0.8061	Intermediate Similarity	NPC44181
0.8061	Intermediate Similarity	NPC53911
0.8061	Intermediate Similarity	NPC471941
0.8061	Intermediate Similarity	NPC193360
0.8058	Intermediate Similarity	NPC477854
0.8056	Intermediate Similarity	NPC241927
0.8056	Intermediate Similarity	NPC258543
0.8041	Intermediate Similarity	NPC473168
0.8041	Intermediate Similarity	NPC327115
0.8041	Intermediate Similarity	NPC469994
0.8041	Intermediate Similarity	NPC51014
0.8041	Intermediate Similarity	NPC20688
0.8039	Intermediate Similarity	NPC192428
0.8039	Intermediate Similarity	NPC477853
0.8039	Intermediate Similarity	NPC173272
0.8037	Intermediate Similarity	NPC144459
0.8037	Intermediate Similarity	NPC185
0.8037	Intermediate Similarity	NPC44063
0.8037	Intermediate Similarity	NPC59530
0.8036	Intermediate Similarity	NPC471854
0.8034	Intermediate Similarity	NPC473265
0.8034	Intermediate Similarity	NPC470882
0.802	Intermediate Similarity	NPC473172
0.8019	Intermediate Similarity	NPC475036
0.8019	Intermediate Similarity	NPC284865
0.8019	Intermediate Similarity	NPC72255
0.8	Intermediate Similarity	NPC473424
0.8	Intermediate Similarity	NPC262870
0.8	Intermediate Similarity	NPC71348
0.8	Intermediate Similarity	NPC100267
0.8	Intermediate Similarity	NPC170487
0.8	Intermediate Similarity	NPC269642
0.8	Intermediate Similarity	NPC475524
0.8	Intermediate Similarity	NPC22388
0.7982	Intermediate Similarity	NPC471406
0.7981	Intermediate Similarity	NPC291785
0.7981	Intermediate Similarity	NPC127408
0.798	Intermediate Similarity	NPC476733
0.798	Intermediate Similarity	NPC54689
0.798	Intermediate Similarity	NPC186688
0.798	Intermediate Similarity	NPC2983
0.798	Intermediate Similarity	NPC215029
0.7965	Intermediate Similarity	NPC475632
0.7965	Intermediate Similarity	NPC311554
0.7965	Intermediate Similarity	NPC86020
0.7965	Intermediate Similarity	NPC257457
0.7963	Intermediate Similarity	NPC469508
0.7961	Intermediate Similarity	NPC473161
0.7961	Intermediate Similarity	NPC190080
0.7961	Intermediate Similarity	NPC107243
0.7961	Intermediate Similarity	NPC57416
0.7961	Intermediate Similarity	NPC111187
0.7959	Intermediate Similarity	NPC96496
0.7949	Intermediate Similarity	NPC198714
0.7946	Intermediate Similarity	NPC270958
0.7944	Intermediate Similarity	NPC278628
0.7944	Intermediate Similarity	NPC231530
0.7941	Intermediate Similarity	NPC200702
0.7941	Intermediate Similarity	NPC127063
0.7941	Intermediate Similarity	NPC138245
0.7941	Intermediate Similarity	NPC231060

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 NPC117185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1729
0.2-0.3	4158
0.3-0.4	2019
0.4-0.5	576
0.5-0.6	168
0.6-0.7	161
0.7-0.8	99
0.8-0.85	56
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD4634	Approved
0.8687	High Similarity	NPD4755	Approved
0.8515	High Similarity	NPD5286	Approved
0.8515	High Similarity	NPD5285	Approved
0.8515	High Similarity	NPD4700	Approved
0.8515	High Similarity	NPD4696	Approved
0.8396	Intermediate Similarity	NPD6372	Approved
0.8396	Intermediate Similarity	NPD6373	Approved
0.8351	Intermediate Similarity	NPD4753	Phase 2
0.835	Intermediate Similarity	NPD5226	Approved
0.835	Intermediate Similarity	NPD5211	Phase 2
0.835	Intermediate Similarity	NPD4633	Approved
0.835	Intermediate Similarity	NPD5225	Approved
0.835	Intermediate Similarity	NPD5224	Approved
0.8304	Intermediate Similarity	NPD6319	Approved
0.8286	Intermediate Similarity	NPD6675	Approved
0.8286	Intermediate Similarity	NPD7128	Approved
0.8286	Intermediate Similarity	NPD4767	Approved
0.8286	Intermediate Similarity	NPD4768	Approved
0.8286	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD5739	Approved
0.8269	Intermediate Similarity	NPD5174	Approved
0.8269	Intermediate Similarity	NPD5175	Approved
0.8252	Intermediate Similarity	NPD5223	Approved
0.8241	Intermediate Similarity	NPD6649	Approved
0.8241	Intermediate Similarity	NPD6650	Approved
0.819	Intermediate Similarity	NPD5141	Approved
0.8165	Intermediate Similarity	NPD8297	Approved
0.8142	Intermediate Similarity	NPD6059	Approved
0.8142	Intermediate Similarity	NPD6054	Approved
0.8131	Intermediate Similarity	NPD7320	Approved
0.8131	Intermediate Similarity	NPD4730	Approved
0.8131	Intermediate Similarity	NPD6899	Approved
0.8131	Intermediate Similarity	NPD4729	Approved
0.8131	Intermediate Similarity	NPD6881	Approved
0.8119	Intermediate Similarity	NPD4629	Approved
0.8119	Intermediate Similarity	NPD5210	Approved
0.8095	Intermediate Similarity	NPD4754	Approved
0.8091	Intermediate Similarity	NPD4632	Approved
0.8039	Intermediate Similarity	NPD4697	Phase 3
0.8037	Intermediate Similarity	NPD5697	Approved
0.8037	Intermediate Similarity	NPD5701	Approved
0.8	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD6882	Approved
0.7982	Intermediate Similarity	NPD7102	Approved
0.7982	Intermediate Similarity	NPD5249	Phase 3
0.7982	Intermediate Similarity	NPD5251	Approved
0.7982	Intermediate Similarity	NPD5250	Approved
0.7982	Intermediate Similarity	NPD5247	Approved
0.7982	Intermediate Similarity	NPD5248	Approved
0.7982	Intermediate Similarity	NPD6883	Approved
0.7982	Intermediate Similarity	NPD7290	Approved
0.798	Intermediate Similarity	NPD5328	Approved
0.7963	Intermediate Similarity	NPD5128	Approved
0.7961	Intermediate Similarity	NPD6083	Phase 2
0.7961	Intermediate Similarity	NPD6084	Phase 2
0.7938	Intermediate Similarity	NPD5329	Approved
0.7921	Intermediate Similarity	NPD4202	Approved
0.7913	Intermediate Similarity	NPD6016	Approved
0.7913	Intermediate Similarity	NPD6015	Approved
0.7909	Intermediate Similarity	NPD6617	Approved
0.7909	Intermediate Similarity	NPD6869	Approved
0.7909	Intermediate Similarity	NPD6847	Approved
0.7909	Intermediate Similarity	NPD8130	Phase 1
0.789	Intermediate Similarity	NPD6013	Approved
0.789	Intermediate Similarity	NPD6012	Approved
0.789	Intermediate Similarity	NPD6014	Approved
0.7864	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD5221	Approved
0.7864	Intermediate Similarity	NPD5222	Approved
0.7863	Intermediate Similarity	NPD7492	Approved
0.7845	Intermediate Similarity	NPD5988	Approved
0.7835	Intermediate Similarity	NPD3666	Approved
0.7835	Intermediate Similarity	NPD3133	Approved
0.7835	Intermediate Similarity	NPD4197	Approved
0.7835	Intermediate Similarity	NPD4786	Approved
0.7835	Intermediate Similarity	NPD3665	Phase 1
0.7822	Intermediate Similarity	NPD6079	Approved
0.7798	Intermediate Similarity	NPD6011	Approved
0.7797	Intermediate Similarity	NPD6616	Approved
0.7788	Intermediate Similarity	NPD5173	Approved
0.7748	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5216	Approved
0.7748	Intermediate Similarity	NPD5215	Approved
0.7748	Intermediate Similarity	NPD5217	Approved
0.7739	Intermediate Similarity	NPD4522	Approved
0.7731	Intermediate Similarity	NPD8293	Discontinued
0.7731	Intermediate Similarity	NPD7078	Approved
0.7719	Intermediate Similarity	NPD6009	Approved
0.7714	Intermediate Similarity	NPD5696	Approved
0.7706	Intermediate Similarity	NPD6412	Phase 2
0.7677	Intermediate Similarity	NPD3618	Phase 1
0.7677	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7736	Approved
0.7658	Intermediate Similarity	NPD5135	Approved
0.7658	Intermediate Similarity	NPD5169	Approved
0.7658	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD4221	Approved
0.7629	Intermediate Similarity	NPD3667	Approved
0.7629	Intermediate Similarity	NPD4223	Phase 3
0.7596	Intermediate Similarity	NPD5695	Phase 3
0.7589	Intermediate Similarity	NPD5127	Approved
0.7573	Intermediate Similarity	NPD6399	Phase 3
0.7521	Intermediate Similarity	NPD6033	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.75	Intermediate Similarity	NPD5279	Phase 3
0.7479	Intermediate Similarity	NPD7604	Phase 2
0.7478	Intermediate Similarity	NPD6274	Approved
0.7458	Intermediate Similarity	NPD5983	Phase 2
0.7455	Intermediate Similarity	NPD6008	Approved
0.7436	Intermediate Similarity	NPD7100	Approved
0.7436	Intermediate Similarity	NPD7101	Approved
0.7391	Intermediate Similarity	NPD5167	Approved
0.7374	Intermediate Similarity	NPD4788	Approved
0.7355	Intermediate Similarity	NPD6336	Discontinued
0.735	Intermediate Similarity	NPD6335	Approved
0.7333	Intermediate Similarity	NPD8328	Phase 3
0.7327	Intermediate Similarity	NPD4688	Approved
0.7327	Intermediate Similarity	NPD6098	Approved
0.7327	Intermediate Similarity	NPD4690	Approved
0.7327	Intermediate Similarity	NPD4693	Phase 3
0.7327	Intermediate Similarity	NPD4689	Approved
0.7327	Intermediate Similarity	NPD4138	Approved
0.7327	Intermediate Similarity	NPD5205	Approved
0.7321	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7319	Approved
0.7311	Intermediate Similarity	NPD6908	Approved
0.7311	Intermediate Similarity	NPD6909	Approved
0.7308	Intermediate Similarity	NPD5284	Approved
0.7308	Intermediate Similarity	NPD5281	Approved
0.7282	Intermediate Similarity	NPD6904	Approved
0.7282	Intermediate Similarity	NPD6080	Approved
0.7282	Intermediate Similarity	NPD6673	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7265	Intermediate Similarity	NPD6317	Approved
0.7245	Intermediate Similarity	NPD7525	Registered
0.7213	Intermediate Similarity	NPD7507	Approved
0.7203	Intermediate Similarity	NPD6313	Approved
0.7203	Intermediate Similarity	NPD6314	Approved
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7168	Intermediate Similarity	NPD5168	Approved
0.7167	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7146	Approved
0.7157	Intermediate Similarity	NPD7521	Approved
0.7157	Intermediate Similarity	NPD7334	Approved
0.7157	Intermediate Similarity	NPD6409	Approved
0.7157	Intermediate Similarity	NPD6684	Approved
0.7157	Intermediate Similarity	NPD5330	Approved
0.7129	Intermediate Similarity	NPD3668	Phase 3
0.7119	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3617	Approved
0.7027	Intermediate Similarity	NPD5091	Approved
0.7019	Intermediate Similarity	NPD6903	Approved
0.7019	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.6984	Remote Similarity	NPD5956	Approved
0.6981	Remote Similarity	NPD6411	Approved
0.6981	Remote Similarity	NPD7515	Phase 2
0.6981	Remote Similarity	NPD5693	Phase 1
0.6981	Remote Similarity	NPD6050	Approved
0.697	Remote Similarity	NPD4195	Approved
0.6947	Remote Similarity	NPD4243	Approved
0.6923	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6053	Discontinued
0.6916	Remote Similarity	NPD5133	Approved
0.6909	Remote Similarity	NPD7638	Approved
0.6907	Remote Similarity	NPD7339	Approved
0.6907	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD5368	Approved
0.69	Remote Similarity	NPD4695	Discontinued
0.6893	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6868	Approved
0.6887	Remote Similarity	NPD5692	Phase 3
0.6852	Remote Similarity	NPD5282	Discontinued
0.6847	Remote Similarity	NPD7639	Approved
0.6847	Remote Similarity	NPD7640	Approved
0.6837	Remote Similarity	NPD6933	Approved
0.6832	Remote Similarity	NPD5369	Approved
0.6822	Remote Similarity	NPD8034	Phase 2
0.6822	Remote Similarity	NPD8035	Phase 2
0.6822	Remote Similarity	NPD5694	Approved
0.6818	Remote Similarity	NPD7902	Approved
0.681	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4785	Approved
0.6804	Remote Similarity	NPD4784	Approved
0.6796	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6101	Approved
0.6765	Remote Similarity	NPD6435	Approved
0.6762	Remote Similarity	NPD7524	Approved
0.6759	Remote Similarity	NPD5779	Approved
0.6759	Remote Similarity	NPD5778	Approved
0.6748	Remote Similarity	NPD6921	Approved
0.6735	Remote Similarity	NPD3703	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data