NPASS Compound

Structure

NPC214644 OpenBabel07101718242D 37 40 0 0 1 0 0 0 0 0999 V2000 2.9855 2.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2424 3.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 1.9292 0.0000 C 0 0 0 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0345 2.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 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 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 O 0 0 0 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3435 1.3795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 0.9511 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 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 6 0 0 0 18 24 1 0 0 0 0 18 31 1 6 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 21 33 2 0 0 0 0 22 29 1 0 0 0 0 22 34 2 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 1 0 0 0 25 36 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 6 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.32
Volume:	544.196
LogP:	2.404
LogD:	2.65
LogS:	-4.255
# Rotatable Bonds:	4
TPSA:	135.29
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.285
Synthetic Accessibility Score:	5.381
Fsp3:	0.8
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:	-4.859
MDCK Permeability:	1.320408955507446e-05
Pgp-inhibitor:	0.948
Pgp-substrate:	0.073
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.29
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.646
Plasma Protein Binding (PPB):	64.554443359375%
Volume Distribution (VD):	0.48
Pgp-substrate:	19.711681365966797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.745
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	3.306
Half-life (T1/2):	0.491

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.153
Carcinogencity:	0.806
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC214644

Natural Product ID:	NPC214644
*Common Name:**	Cucurbitacin F
IUPAC Name:	(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
Synonyms:	Cucurbitacin F
Standard InCHIKey:	AOHIGMQGPFTKQX-QZPKXHNASA-N
Standard InCHI:	InChI=1S/C30H46O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17-20,23-24,31-32,35-37H,10,13-15H2,1-8H3/b12-11+/t17-,18+,19-,20+,23+,24-,27+,28-,29+,30+/m1/s1
SMILES:	CC(C)(/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@@H]([C@H](C4(C)C)O)O)[C@]3(C)C(=O)C[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488312
PubChem CID:	5281320
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
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33269591]
NPO12307	Elaeocarpus dolichostylus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6549470]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12307	Elaeocarpus dolichostylus	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
EC50	1
ED50	2
IC50	1
Others	1

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	0.16	ug.mL-1	PMID[448041]
NPT759	Cell Line	H9	Homo sapiens	EC50	=	0.06	ug.mL-1	PMID[448041]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.074	ug ml-1	PMID[448042]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.04	ug ml-1	PMID[448042]
NPT2	Others	Unspecified		Therapeutic index	=	2.7	n.a.	PMID[448041]

☑ 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 NPC214644 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	201
0.1-0.2	1233
0.2-0.3	4171
0.3-0.4	8831
0.4-0.5	12774
0.5-0.6	7207
0.6-0.7	5823
0.7-0.8	2179
0.8-0.85	190
0.85-0.9	43
0.9-0.95	42
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC311612
0.9412	High Similarity	NPC185
0.94	High Similarity	NPC87351
0.94	High Similarity	NPC477915
0.9346	High Similarity	NPC471854
0.9314	High Similarity	NPC149047
0.9245	High Similarity	NPC73300
0.9245	High Similarity	NPC108721
0.9223	High Similarity	NPC220229
0.9223	High Similarity	NPC475060
0.9223	High Similarity	NPC83744
0.9223	High Similarity	NPC477916
0.9216	High Similarity	NPC204833
0.9216	High Similarity	NPC209502
0.9208	High Similarity	NPC473424
0.9135	High Similarity	NPC217201
0.9135	High Similarity	NPC329417
0.9126	High Similarity	NPC257353
0.9126	High Similarity	NPC319077
0.9126	High Similarity	NPC476027
0.9126	High Similarity	NPC214264
0.9126	High Similarity	NPC296945
0.9126	High Similarity	NPC171137
0.9126	High Similarity	NPC152695
0.9126	High Similarity	NPC49958
0.9126	High Similarity	NPC302607
0.9126	High Similarity	NPC48733
0.9126	High Similarity	NPC202167
0.9126	High Similarity	NPC85829
0.9126	High Similarity	NPC260268
0.9126	High Similarity	NPC50692
0.9126	High Similarity	NPC97202
0.9126	High Similarity	NPC150531
0.9118	High Similarity	NPC191892
0.9118	High Similarity	NPC111323
0.9083	High Similarity	NPC257457
0.9083	High Similarity	NPC311554
0.9048	High Similarity	NPC11710
0.901	High Similarity	NPC144956
0.8952	High Similarity	NPC65941
0.8932	High Similarity	NPC249187
0.8932	High Similarity	NPC247957
0.8857	High Similarity	NPC165873
0.8812	High Similarity	NPC18509
0.8796	High Similarity	NPC207251
0.8785	High Similarity	NPC76084
0.8762	High Similarity	NPC166607
0.8716	High Similarity	NPC317210
0.8713	High Similarity	NPC471463
0.8713	High Similarity	NPC249954
0.87	High Similarity	NPC472977
0.87	High Similarity	NPC472976
0.8667	High Similarity	NPC72255
0.8667	High Similarity	NPC160843
0.8667	High Similarity	NPC137657
0.8641	High Similarity	NPC154072
0.8636	High Similarity	NPC326542
0.8627	High Similarity	NPC474785
0.8627	High Similarity	NPC474938
0.8624	High Similarity	NPC475524
0.8624	High Similarity	NPC100267
0.8614	High Similarity	NPC259286
0.8614	High Similarity	NPC472932
0.8614	High Similarity	NPC473170
0.8611	High Similarity	NPC235077
0.86	High Similarity	NPC474736
0.86	High Similarity	NPC109305
0.8596	High Similarity	NPC222688
0.8571	High Similarity	NPC329736
0.8559	High Similarity	NPC148458
0.8545	High Similarity	NPC962
0.8545	High Similarity	NPC250109
0.8529	High Similarity	NPC49371
0.8529	High Similarity	NPC117133
0.8515	High Similarity	NPC8993
0.8505	High Similarity	NPC44063
0.85	High Similarity	NPC472978
0.85	High Similarity	NPC475806
0.85	High Similarity	NPC168027
0.85	High Similarity	NPC185936
0.8496	Intermediate Similarity	NPC473270
0.8496	Intermediate Similarity	NPC61520
0.8491	Intermediate Similarity	NPC75531
0.8491	Intermediate Similarity	NPC149124
0.8468	Intermediate Similarity	NPC67259
0.8468	Intermediate Similarity	NPC147912
0.8462	Intermediate Similarity	NPC474720
0.8462	Intermediate Similarity	NPC316964
0.8462	Intermediate Similarity	NPC470882
0.8462	Intermediate Similarity	NPC110149
0.8455	Intermediate Similarity	NPC280782
0.8431	Intermediate Similarity	NPC180950
0.8431	Intermediate Similarity	NPC271195
0.8426	Intermediate Similarity	NPC177064
0.8426	Intermediate Similarity	NPC295244
0.8421	Intermediate Similarity	NPC109973
0.8416	Intermediate Similarity	NPC69454
0.8416	Intermediate Similarity	NPC472930
0.8411	Intermediate Similarity	NPC323834
0.8411	Intermediate Similarity	NPC60681
0.84	Intermediate Similarity	NPC48010
0.8396	Intermediate Similarity	NPC117185
0.8396	Intermediate Similarity	NPC26478
0.8393	Intermediate Similarity	NPC266728
0.8393	Intermediate Similarity	NPC49492
0.8393	Intermediate Similarity	NPC270929
0.8381	Intermediate Similarity	NPC302537
0.8381	Intermediate Similarity	NPC163372
0.8365	Intermediate Similarity	NPC103051
0.8365	Intermediate Similarity	NPC197386
0.835	Intermediate Similarity	NPC192428
0.8349	Intermediate Similarity	NPC2766
0.8333	Intermediate Similarity	NPC475294
0.8333	Intermediate Similarity	NPC245972
0.8333	Intermediate Similarity	NPC58370
0.8333	Intermediate Similarity	NPC144459
0.8333	Intermediate Similarity	NPC474690
0.8333	Intermediate Similarity	NPC475041
0.8333	Intermediate Similarity	NPC43285
0.8333	Intermediate Similarity	NPC196485
0.8333	Intermediate Similarity	NPC472925
0.8333	Intermediate Similarity	NPC264954
0.8333	Intermediate Similarity	NPC292793
0.8333	Intermediate Similarity	NPC299100
0.8319	Intermediate Similarity	NPC470959
0.8319	Intermediate Similarity	NPC476965
0.8319	Intermediate Similarity	NPC239273
0.8317	Intermediate Similarity	NPC155304
0.8317	Intermediate Similarity	NPC63748
0.8317	Intermediate Similarity	NPC473998
0.8305	Intermediate Similarity	NPC473253
0.8305	Intermediate Similarity	NPC473265
0.8302	Intermediate Similarity	NPC136289
0.8302	Intermediate Similarity	NPC204450
0.8302	Intermediate Similarity	NPC308726
0.8302	Intermediate Similarity	NPC185530
0.8302	Intermediate Similarity	NPC119601
0.8302	Intermediate Similarity	NPC195290
0.83	Intermediate Similarity	NPC326627
0.83	Intermediate Similarity	NPC310010
0.83	Intermediate Similarity	NPC31985
0.83	Intermediate Similarity	NPC1015
0.83	Intermediate Similarity	NPC309603
0.83	Intermediate Similarity	NPC473999
0.83	Intermediate Similarity	NPC477943
0.83	Intermediate Similarity	NPC2983
0.83	Intermediate Similarity	NPC474245
0.83	Intermediate Similarity	NPC472973
0.83	Intermediate Similarity	NPC76879
0.83	Intermediate Similarity	NPC32830
0.8288	Intermediate Similarity	NPC221144
0.8288	Intermediate Similarity	NPC71348
0.8286	Intermediate Similarity	NPC15390
0.8269	Intermediate Similarity	NPC161147
0.8261	Intermediate Similarity	NPC474370
0.8252	Intermediate Similarity	NPC200702
0.8252	Intermediate Similarity	NPC472824
0.8252	Intermediate Similarity	NPC272617
0.8235	Intermediate Similarity	NPC472496
0.8235	Intermediate Similarity	NPC233118
0.8224	Intermediate Similarity	NPC475050
0.8224	Intermediate Similarity	NPC264048
0.8224	Intermediate Similarity	NPC236390
0.8218	Intermediate Similarity	NPC320026
0.8208	Intermediate Similarity	NPC81530
0.8208	Intermediate Similarity	NPC476897
0.8208	Intermediate Similarity	NPC224720
0.8208	Intermediate Similarity	NPC476223
0.8208	Intermediate Similarity	NPC476240
0.8205	Intermediate Similarity	NPC473979
0.82	Intermediate Similarity	NPC328539
0.82	Intermediate Similarity	NPC158778
0.8198	Intermediate Similarity	NPC472928
0.8198	Intermediate Similarity	NPC43775
0.819	Intermediate Similarity	NPC473256
0.819	Intermediate Similarity	NPC470878
0.819	Intermediate Similarity	NPC114274
0.8182	Intermediate Similarity	NPC470257
0.8182	Intermediate Similarity	NPC471855
0.8182	Intermediate Similarity	NPC163004
0.8173	Intermediate Similarity	NPC305483
0.8173	Intermediate Similarity	NPC96859
0.8173	Intermediate Similarity	NPC328162
0.8167	Intermediate Similarity	NPC470880
0.8158	Intermediate Similarity	NPC470492
0.8158	Intermediate Similarity	NPC167606
0.8158	Intermediate Similarity	NPC286528
0.8158	Intermediate Similarity	NPC20302
0.8158	Intermediate Similarity	NPC140055
0.8155	Intermediate Similarity	NPC473172
0.8155	Intermediate Similarity	NPC473162
0.8155	Intermediate Similarity	NPC196227
0.8155	Intermediate Similarity	NPC111015
0.8148	Intermediate Similarity	NPC235889
0.8137	Intermediate Similarity	NPC116726
0.8137	Intermediate Similarity	NPC272746
0.8136	Intermediate Similarity	NPC473255
0.8136	Intermediate Similarity	NPC172154
0.8136	Intermediate Similarity	NPC81736
0.8125	Intermediate Similarity	NPC264634

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 NPC214644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1457
0.2-0.3	3847
0.3-0.4	2463
0.4-0.5	712
0.5-0.6	170
0.6-0.7	160
0.7-0.8	89
0.8-0.85	47
0.85-0.9	23
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9208	High Similarity	NPD5211	Phase 2
0.9029	High Similarity	NPD5141	Approved
0.901	High Similarity	NPD4696	Approved
0.901	High Similarity	NPD5285	Approved
0.901	High Similarity	NPD5286	Approved
0.8835	High Similarity	NPD4633	Approved
0.8835	High Similarity	NPD5226	Approved
0.8835	High Similarity	NPD5224	Approved
0.8835	High Similarity	NPD5225	Approved
0.8812	High Similarity	NPD4755	Approved
0.875	High Similarity	NPD5175	Approved
0.875	High Similarity	NPD5174	Approved
0.8738	High Similarity	NPD5223	Approved
0.8641	High Similarity	NPD4700	Approved
0.8611	High Similarity	NPD4634	Approved
0.8598	High Similarity	NPD6881	Approved
0.8598	High Similarity	NPD6899	Approved
0.8532	High Similarity	NPD6649	Approved
0.8532	High Similarity	NPD6650	Approved
0.8529	High Similarity	NPD5221	Approved
0.8529	High Similarity	NPD5220	Clinical (unspecified phase)
0.8529	High Similarity	NPD5222	Approved
0.8505	High Similarity	NPD5697	Approved
0.85	High Similarity	NPD6079	Approved
0.8455	Intermediate Similarity	NPD8297	Approved
0.8447	Intermediate Similarity	NPD5173	Approved
0.844	Intermediate Similarity	NPD7102	Approved
0.844	Intermediate Similarity	NPD6883	Approved
0.844	Intermediate Similarity	NPD7290	Approved
0.8431	Intermediate Similarity	NPD4629	Approved
0.8431	Intermediate Similarity	NPD5210	Approved
0.8426	Intermediate Similarity	NPD4730	Approved
0.8426	Intermediate Similarity	NPD4729	Approved
0.8411	Intermediate Similarity	NPD5739	Approved
0.8411	Intermediate Similarity	NPD7128	Approved
0.8411	Intermediate Similarity	NPD6675	Approved
0.8411	Intermediate Similarity	NPD6402	Approved
0.8364	Intermediate Similarity	NPD8130	Phase 1
0.8364	Intermediate Similarity	NPD6869	Approved
0.8364	Intermediate Similarity	NPD6847	Approved
0.8364	Intermediate Similarity	NPD6617	Approved
0.835	Intermediate Similarity	NPD4697	Phase 3
0.8349	Intermediate Similarity	NPD6372	Approved
0.8349	Intermediate Similarity	NPD6013	Approved
0.8349	Intermediate Similarity	NPD6014	Approved
0.8349	Intermediate Similarity	NPD6012	Approved
0.8349	Intermediate Similarity	NPD6373	Approved
0.83	Intermediate Similarity	NPD5328	Approved
0.83	Intermediate Similarity	NPD4753	Phase 2
0.8288	Intermediate Similarity	NPD6882	Approved
0.8273	Intermediate Similarity	NPD5250	Approved
0.8273	Intermediate Similarity	NPD5247	Approved
0.8273	Intermediate Similarity	NPD5248	Approved
0.8273	Intermediate Similarity	NPD5249	Phase 3
0.8273	Intermediate Similarity	NPD5251	Approved
0.8257	Intermediate Similarity	NPD7320	Approved
0.8257	Intermediate Similarity	NPD5128	Approved
0.8257	Intermediate Similarity	NPD6011	Approved
0.8241	Intermediate Similarity	NPD4767	Approved
0.8241	Intermediate Similarity	NPD4768	Approved
0.8224	Intermediate Similarity	NPD4754	Approved
0.8214	Intermediate Similarity	NPD4632	Approved
0.8198	Intermediate Similarity	NPD5217	Approved
0.8198	Intermediate Similarity	NPD5215	Approved
0.8198	Intermediate Similarity	NPD5216	Approved
0.8165	Intermediate Similarity	NPD5701	Approved
0.8158	Intermediate Similarity	NPD7115	Discovery
0.8108	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD5135	Approved
0.8108	Intermediate Similarity	NPD5169	Approved
0.8058	Intermediate Similarity	NPD4202	Approved
0.8036	Intermediate Similarity	NPD5127	Approved
0.8	Intermediate Similarity	NPD3618	Phase 1
0.7949	Intermediate Similarity	NPD6319	Approved
0.7949	Intermediate Similarity	NPD6054	Approved
0.7925	Intermediate Similarity	NPD6084	Phase 2
0.7925	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD5329	Approved
0.7876	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD7101	Approved
0.7863	Intermediate Similarity	NPD7100	Approved
0.7845	Intermediate Similarity	NPD6009	Approved
0.7826	Intermediate Similarity	NPD5167	Approved
0.7822	Intermediate Similarity	NPD5690	Phase 2
0.7815	Intermediate Similarity	NPD6370	Approved
0.78	Intermediate Similarity	NPD4197	Approved
0.78	Intermediate Similarity	NPD3665	Phase 1
0.78	Intermediate Similarity	NPD3133	Approved
0.78	Intermediate Similarity	NPD4786	Approved
0.78	Intermediate Similarity	NPD3666	Approved
0.7778	Intermediate Similarity	NPD6335	Approved
0.7768	Intermediate Similarity	NPD5168	Approved
0.7759	Intermediate Similarity	NPD6274	Approved
0.7731	Intermediate Similarity	NPD6015	Approved
0.7731	Intermediate Similarity	NPD6016	Approved
0.7692	Intermediate Similarity	NPD6317	Approved
0.7686	Intermediate Similarity	NPD7492	Approved
0.7685	Intermediate Similarity	NPD5696	Approved
0.7667	Intermediate Similarity	NPD5988	Approved
0.7647	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6059	Approved
0.7627	Intermediate Similarity	NPD6314	Approved
0.7627	Intermediate Similarity	NPD6313	Approved
0.7623	Intermediate Similarity	NPD6616	Approved
0.7603	Intermediate Similarity	NPD7604	Phase 2
0.76	Intermediate Similarity	NPD4221	Approved
0.76	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD4223	Phase 3
0.7583	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5983	Phase 2
0.757	Intermediate Similarity	NPD5695	Phase 3
0.7561	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.748	Intermediate Similarity	NPD6336	Discontinued
0.7476	Intermediate Similarity	NPD5280	Approved
0.7476	Intermediate Similarity	NPD5279	Phase 3
0.7476	Intermediate Similarity	NPD4694	Approved
0.7458	Intermediate Similarity	NPD6868	Approved
0.7438	Intermediate Similarity	NPD6909	Approved
0.7438	Intermediate Similarity	NPD6908	Approved
0.7434	Intermediate Similarity	NPD6008	Approved
0.7383	Intermediate Similarity	NPD6399	Phase 3
0.7353	Intermediate Similarity	NPD4788	Approved
0.7321	Intermediate Similarity	NPD5091	Approved
0.7308	Intermediate Similarity	NPD4693	Phase 3
0.7308	Intermediate Similarity	NPD4138	Approved
0.7308	Intermediate Similarity	NPD4689	Approved
0.7308	Intermediate Similarity	NPD5205	Approved
0.7308	Intermediate Similarity	NPD4688	Approved
0.7308	Intermediate Similarity	NPD4690	Approved
0.73	Intermediate Similarity	NPD4195	Approved
0.7297	Intermediate Similarity	NPD7640	Approved
0.7297	Intermediate Similarity	NPD7639	Approved
0.729	Intermediate Similarity	NPD7515	Phase 2
0.729	Intermediate Similarity	NPD5281	Approved
0.729	Intermediate Similarity	NPD5284	Approved
0.728	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD4522	Approved
0.7264	Intermediate Similarity	NPD6080	Approved
0.7264	Intermediate Similarity	NPD6904	Approved
0.7264	Intermediate Similarity	NPD6673	Approved
0.7248	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4695	Discontinued
0.7217	Intermediate Similarity	NPD6412	Phase 2
0.7207	Intermediate Similarity	NPD4225	Approved
0.7207	Intermediate Similarity	NPD7638	Approved
0.72	Intermediate Similarity	NPD7507	Approved
0.717	Intermediate Similarity	NPD6672	Approved
0.717	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD4519	Discontinued
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD4623	Approved
0.713	Intermediate Similarity	NPD5693	Phase 1
0.7115	Intermediate Similarity	NPD3668	Phase 3
0.7087	Intermediate Similarity	NPD6033	Approved
0.7075	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7525	Registered
0.7048	Intermediate Similarity	NPD1696	Phase 3
0.7048	Intermediate Similarity	NPD5363	Approved
0.7037	Intermediate Similarity	NPD5785	Approved
0.7031	Intermediate Similarity	NPD7319	Approved
0.703	Intermediate Similarity	NPD3617	Approved
0.7009	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6903	Approved
0.7009	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7748	Approved
0.6981	Remote Similarity	NPD6098	Approved
0.6972	Remote Similarity	NPD6050	Approved
0.6972	Remote Similarity	NPD5694	Approved
0.6964	Remote Similarity	NPD7902	Approved
0.6917	Remote Similarity	NPD6053	Discontinued
0.6916	Remote Similarity	NPD3573	Approved
0.6909	Remote Similarity	NPD5133	Approved
0.69	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD7339	Approved
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5692	Phase 3
0.6852	Remote Similarity	NPD4518	Approved
0.6847	Remote Similarity	NPD6001	Approved
0.6822	Remote Similarity	NPD5786	Approved
0.6807	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4785	Approved
0.68	Remote Similarity	NPD4784	Approved
0.678	Remote Similarity	NPD6614	Approved
0.6772	Remote Similarity	NPD8328	Phase 3
0.6762	Remote Similarity	NPD4270	Approved
0.6762	Remote Similarity	NPD4269	Approved
0.6759	Remote Similarity	NPD7524	Approved
0.6746	Remote Similarity	NPD7503	Approved
0.6738	Remote Similarity	NPD7236	Approved
0.6731	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4096	Approved
0.6727	Remote Similarity	NPD5207	Approved
0.6724	Remote Similarity	NPD7632	Discontinued

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