NPASS Compound

Structure

NPC261266 OpenBabel07101719142D 34 37 0 0 1 0 0 0 0 0999 V2000 2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9792 5.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2361 4.4223 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 -2.9641 -3.8660 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 -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 0.9000 2.9543 0.0000 C 0 0 0 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 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 1.8781 3.1622 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 -1.7321 -3.0000 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 1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1871 4.1132 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 -1.7321 -1.0000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 4.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 17 28 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 27 1 0 0 0 0 23 32 1 1 0 0 0 24 30 1 1 0 0 0 24 33 1 0 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 26 34 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	523.098
LogP:	5.003
LogD:	4.189
LogS:	-4.498
# Rotatable Bonds:	4
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	5.346
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822
MDCK Permeability:	1.691295619821176e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.496
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.158

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318
Plasma Protein Binding (PPB):	89.42091369628906%
Volume Distribution (VD):	0.667
Pgp-substrate:	8.256322860717773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.553
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	6.478
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.217
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC261266

Natural Product ID:	NPC261266
*Common Name:**	Cucurbalsaminol A
IUPAC Name:	(3S,7S,8R,9S,10S,12R,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
Synonyms:
Standard InCHIKey:	WFULNIMUTJQIKF-HCLZVIJHSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-18(10-9-14-26(2,3)34)19-13-15-29(7)25-22(31)16-21-20(11-12-23(32)27(21,4)5)28(25,6)17-24(33)30(19,29)8/h9,14,16,18-20,22-25,31-34H,10-13,15,17H2,1-8H3/b14-9+/t18-,19-,20-,22+,23+,24-,25-,28+,29+,30+/m1/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)[C@H](O)C[C@@]1([C@H]2[C@@H](O)C=C2[C@H]1CC[C@@H](C2(C)C)O)C)C)C/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077876
PubChem CID:	44607278
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
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	African	n.a.	PMID[19795842]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20541427]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31339732]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	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	6
Others	10

Activity Type	# Activity
Cell Line	2
Individual Protein	8
NON-MOLECULAR	2
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	133300.0	nM	PMID[488248]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	133300.0	nM	PMID[488249]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	13200.0	nM	PMID[488249]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	17600.0	nM	PMID[488249]
NPT2	Others	Unspecified		Selectivity Index	>	10.1	n.a.	PMID[488249]
NPT2	Others	Unspecified		Selectivity Index	>	7.6	n.a.	PMID[488249]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	63400.0	nM	PMID[488250]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48200.0	nM	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	427.2	n.a.	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	429.0	n.a.	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	254.7	n.a.	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	252.0	n.a.	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	8.8	n.a.	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	38.2	n.a.	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.7	n.a.	PMID[488250]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	2.9	n.a.	PMID[488250]

☑ 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 NPC261266 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	166
0.1-0.2	1303
0.2-0.3	4762
0.3-0.4	13873
0.4-0.5	9839
0.5-0.6	5952
0.6-0.7	4784
0.7-0.8	1602
0.8-0.85	250
0.85-0.9	112
0.9-0.95	48
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9753	High Similarity	NPC6391
0.9524	High Similarity	NPC295668
0.9506	High Similarity	NPC205845
0.95	High Similarity	NPC50964
0.95	High Similarity	NPC49964
0.9412	High Similarity	NPC97404
0.9412	High Similarity	NPC41554
0.939	High Similarity	NPC470360
0.9375	High Similarity	NPC209620
0.9375	High Similarity	NPC23852
0.9375	High Similarity	NPC264245
0.9294	High Similarity	NPC204188
0.9294	High Similarity	NPC11216
0.9294	High Similarity	NPC3345
0.9294	High Similarity	NPC80561
0.9294	High Similarity	NPC329596
0.9294	High Similarity	NPC291484
0.9286	High Similarity	NPC474668
0.9286	High Similarity	NPC133588
0.9277	High Similarity	NPC299068
0.9277	High Similarity	NPC152808
0.9277	High Similarity	NPC293287
0.9259	High Similarity	NPC87489
0.9259	High Similarity	NPC296701
0.9259	High Similarity	NPC218616
0.9259	High Similarity	NPC101462
0.925	High Similarity	NPC209944
0.925	High Similarity	NPC234193
0.925	High Similarity	NPC241290
0.925	High Similarity	NPC164840
0.9176	High Similarity	NPC470361
0.9167	High Similarity	NPC149224
0.9157	High Similarity	NPC318390
0.9157	High Similarity	NPC274448
0.9146	High Similarity	NPC474634
0.9136	High Similarity	NPC476646
0.9136	High Similarity	NPC47761
0.9125	High Similarity	NPC109546
0.9125	High Similarity	NPC209430
0.9125	High Similarity	NPC30986
0.9125	High Similarity	NPC143182
0.9125	High Similarity	NPC84694
0.9125	High Similarity	NPC28862
0.9125	High Similarity	NPC47982
0.9125	High Similarity	NPC81306
0.9048	High Similarity	NPC139724
0.9036	High Similarity	NPC231310
0.9036	High Similarity	NPC470077
0.9036	High Similarity	NPC238485
0.9036	High Similarity	NPC185568
0.9036	High Similarity	NPC124172
0.9012	High Similarity	NPC96362
0.9	High Similarity	NPC87604
0.9	High Similarity	NPC474216
0.8989	High Similarity	NPC288970
0.8929	High Similarity	NPC266511
0.8929	High Similarity	NPC157257
0.8916	High Similarity	NPC475789
0.8916	High Similarity	NPC317458
0.8916	High Similarity	NPC82623
0.8902	High Similarity	NPC470383
0.8902	High Similarity	NPC249423
0.8875	High Similarity	NPC318495
0.8875	High Similarity	NPC91594
0.8875	High Similarity	NPC471798
0.8875	High Similarity	NPC155986
0.8875	High Similarity	NPC198968
0.8864	High Similarity	NPC310013
0.8851	High Similarity	NPC245410
0.8851	High Similarity	NPC270511
0.8851	High Similarity	NPC14380
0.8851	High Similarity	NPC192437
0.8851	High Similarity	NPC470390
0.8837	High Similarity	NPC280556
0.8824	High Similarity	NPC94462
0.8824	High Similarity	NPC24277
0.881	High Similarity	NPC475798
0.881	High Similarity	NPC474493
0.881	High Similarity	NPC209802
0.881	High Similarity	NPC474047
0.881	High Similarity	NPC127606
0.8795	High Similarity	NPC1272
0.8795	High Similarity	NPC30166
0.8795	High Similarity	NPC202389
0.8795	High Similarity	NPC248886
0.8795	High Similarity	NPC470049
0.8795	High Similarity	NPC189972
0.8795	High Similarity	NPC470614
0.878	High Similarity	NPC102253
0.878	High Similarity	NPC26117
0.878	High Similarity	NPC322313
0.878	High Similarity	NPC236237
0.8765	High Similarity	NPC275910
0.8765	High Similarity	NPC473943
0.8765	High Similarity	NPC285761
0.8764	High Similarity	NPC65402
0.8764	High Similarity	NPC279410
0.8764	High Similarity	NPC144202
0.8764	High Similarity	NPC127718
0.8764	High Similarity	NPC119562
0.875	High Similarity	NPC189883
0.875	High Similarity	NPC240604
0.875	High Similarity	NPC244488
0.875	High Similarity	NPC134330
0.875	High Similarity	NPC253190
0.875	High Similarity	NPC247325
0.875	High Similarity	NPC265588
0.875	High Similarity	NPC129165
0.875	High Similarity	NPC300324
0.875	High Similarity	NPC113733
0.875	High Similarity	NPC321016
0.875	High Similarity	NPC321381
0.875	High Similarity	NPC107059
0.875	High Similarity	NPC275671
0.8736	High Similarity	NPC101886
0.869	High Similarity	NPC110778
0.869	High Similarity	NPC470558
0.869	High Similarity	NPC193870
0.869	High Similarity	NPC470384
0.869	High Similarity	NPC134481
0.869	High Similarity	NPC141941
0.869	High Similarity	NPC477818
0.8681	High Similarity	NPC99726
0.8675	High Similarity	NPC474683
0.8675	High Similarity	NPC474731
0.8675	High Similarity	NPC474752
0.8675	High Similarity	NPC7505
0.8675	High Similarity	NPC474531
0.8675	High Similarity	NPC82986
0.8675	High Similarity	NPC474759
0.8667	High Similarity	NPC8774
0.8659	High Similarity	NPC328714
0.8659	High Similarity	NPC273410
0.8659	High Similarity	NPC1319
0.8659	High Similarity	NPC80530
0.8659	High Similarity	NPC472463
0.8652	High Similarity	NPC27531
0.8642	High Similarity	NPC470758
0.8642	High Similarity	NPC214570
0.8642	High Similarity	NPC470711
0.8625	High Similarity	NPC230301
0.8625	High Similarity	NPC304309
0.8625	High Similarity	NPC141071
0.8625	High Similarity	NPC285893
0.8625	High Similarity	NPC288035
0.8625	High Similarity	NPC32832
0.8625	High Similarity	NPC134847
0.8625	High Similarity	NPC136188
0.8625	High Similarity	NPC22105
0.8625	High Similarity	NPC257347
0.8625	High Similarity	NPC471723
0.8625	High Similarity	NPC162742
0.8625	High Similarity	NPC28657
0.8621	High Similarity	NPC212596
0.8621	High Similarity	NPC67872
0.8621	High Similarity	NPC475605
0.8621	High Similarity	NPC470542
0.8621	High Similarity	NPC4574
0.8605	High Similarity	NPC201273
0.8605	High Similarity	NPC6605
0.8571	High Similarity	NPC7988
0.8571	High Similarity	NPC276103
0.8571	High Similarity	NPC54248
0.8571	High Similarity	NPC98457
0.8571	High Similarity	NPC227583
0.8571	High Similarity	NPC12103
0.8571	High Similarity	NPC72204
0.8556	High Similarity	NPC474922
0.8556	High Similarity	NPC292793
0.8556	High Similarity	NPC477605
0.8554	High Similarity	NPC236112
0.8554	High Similarity	NPC13554
0.8537	High Similarity	NPC477522
0.8537	High Similarity	NPC167891
0.8537	High Similarity	NPC18603
0.8537	High Similarity	NPC11908
0.8537	High Similarity	NPC6978
0.8537	High Similarity	NPC244385
0.8537	High Similarity	NPC307965
0.8537	High Similarity	NPC83351
0.8537	High Similarity	NPC76931
0.8537	High Similarity	NPC167037
0.8537	High Similarity	NPC301707
0.8537	High Similarity	NPC138621
0.8523	High Similarity	NPC105495
0.8523	High Similarity	NPC138974
0.8523	High Similarity	NPC477606
0.8519	High Similarity	NPC237460
0.8519	High Similarity	NPC46160
0.8519	High Similarity	NPC202642
0.8519	High Similarity	NPC470749
0.8519	High Similarity	NPC73875
0.8519	High Similarity	NPC470362
0.8506	High Similarity	NPC470620
0.8506	High Similarity	NPC304083
0.8506	High Similarity	NPC475313
0.85	High Similarity	NPC201048
0.85	High Similarity	NPC477138
0.85	High Similarity	NPC306727
0.85	High Similarity	NPC243342

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 NPC261266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1458
0.2-0.3	4103
0.3-0.4	2382
0.4-0.5	585
0.5-0.6	193
0.6-0.7	176
0.7-0.8	81
0.8-0.85	16
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD7525	Registered
0.8721	High Similarity	NPD4751	Clinical (unspecified phase)
0.8625	High Similarity	NPD6942	Approved
0.8625	High Similarity	NPD7339	Approved
0.8333	Intermediate Similarity	NPD6931	Approved
0.8333	Intermediate Similarity	NPD6930	Phase 2
0.8333	Intermediate Similarity	NPD7514	Phase 3
0.8293	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6695	Phase 3
0.8214	Intermediate Similarity	NPD6929	Approved
0.8161	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7332	Phase 2
0.8095	Intermediate Similarity	NPD7145	Approved
0.8049	Intermediate Similarity	NPD4784	Approved
0.8049	Intermediate Similarity	NPD6926	Approved
0.8049	Intermediate Similarity	NPD4785	Approved
0.8049	Intermediate Similarity	NPD6924	Approved
0.8023	Intermediate Similarity	NPD6902	Approved
0.7976	Intermediate Similarity	NPD6932	Approved
0.7976	Intermediate Similarity	NPD6925	Approved
0.7976	Intermediate Similarity	NPD5776	Phase 2
0.7955	Intermediate Similarity	NPD4786	Approved
0.7889	Intermediate Similarity	NPD7524	Approved
0.7889	Intermediate Similarity	NPD7750	Discontinued
0.7882	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6893	Approved
0.7857	Intermediate Similarity	NPD6933	Approved
0.7805	Intermediate Similarity	NPD7150	Approved
0.7805	Intermediate Similarity	NPD7152	Approved
0.7805	Intermediate Similarity	NPD4243	Approved
0.7805	Intermediate Similarity	NPD7151	Approved
0.7791	Intermediate Similarity	NPD7645	Phase 2
0.7742	Intermediate Similarity	NPD6079	Approved
0.7738	Intermediate Similarity	NPD8264	Approved
0.7732	Intermediate Similarity	NPD7639	Approved
0.7732	Intermediate Similarity	NPD7640	Approved
0.7727	Intermediate Similarity	NPD3667	Approved
0.7717	Intermediate Similarity	NPD5328	Approved
0.7701	Intermediate Similarity	NPD4748	Discontinued
0.7683	Intermediate Similarity	NPD7144	Approved
0.7683	Intermediate Similarity	NPD7143	Approved
0.7629	Intermediate Similarity	NPD7638	Approved
0.7614	Intermediate Similarity	NPD6898	Phase 1
0.7586	Intermediate Similarity	NPD6683	Phase 2
0.7582	Intermediate Similarity	NPD3618	Phase 1
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7561	Intermediate Similarity	NPD6923	Approved
0.7561	Intermediate Similarity	NPD6922	Approved
0.7553	Intermediate Similarity	NPD7087	Discontinued
0.75	Intermediate Similarity	NPD7509	Discontinued
0.7474	Intermediate Similarity	NPD4202	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7423	Intermediate Similarity	NPD5222	Approved
0.7423	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5221	Approved
0.7386	Intermediate Similarity	NPD4195	Approved
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.7368	Intermediate Similarity	NPD7637	Suspended
0.7347	Intermediate Similarity	NPD5173	Approved
0.7347	Intermediate Similarity	NPD4755	Approved
0.7326	Intermediate Similarity	NPD5275	Approved
0.7326	Intermediate Similarity	NPD4190	Phase 3
0.73	Intermediate Similarity	NPD5223	Approved
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7245	Intermediate Similarity	NPD4697	Phase 3
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD4700	Approved
0.7174	Intermediate Similarity	NPD3668	Phase 3
0.7174	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD3666	Approved
0.7174	Intermediate Similarity	NPD3133	Approved
0.7158	Intermediate Similarity	NPD6051	Approved
0.7158	Intermediate Similarity	NPD4753	Phase 2
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7156	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7136	Phase 2
0.7075	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD7128	Approved
0.7019	Intermediate Similarity	NPD6675	Approved
0.7019	Intermediate Similarity	NPD6402	Approved
0.7019	Intermediate Similarity	NPD5739	Approved
0.701	Intermediate Similarity	NPD7515	Phase 2
0.699	Remote Similarity	NPD4754	Approved
0.697	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD5210	Approved
0.6957	Remote Similarity	NPD4223	Phase 3
0.6957	Remote Similarity	NPD4221	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6931	Remote Similarity	NPD5290	Discontinued
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6915	Remote Similarity	NPD5329	Approved
0.6914	Remote Similarity	NPD368	Approved
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.6887	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD7320	Approved
0.6881	Remote Similarity	NPD4632	Approved
0.6857	Remote Similarity	NPD4768	Approved
0.6857	Remote Similarity	NPD4767	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD5279	Phase 3
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4519	Discontinued
0.6832	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD6083	Phase 2
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6373	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6372	Approved
0.6809	Remote Similarity	NPD4197	Approved
0.6796	Remote Similarity	NPD4159	Approved
0.6792	Remote Similarity	NPD5701	Approved
0.6789	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6786	Remote Similarity	NPD7328	Approved
0.6786	Remote Similarity	NPD7327	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6759	Remote Similarity	NPD5249	Phase 3
0.6759	Remote Similarity	NPD5169	Approved
0.6759	Remote Similarity	NPD5250	Approved
0.6759	Remote Similarity	NPD5251	Approved
0.6759	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5135	Approved
0.6759	Remote Similarity	NPD5247	Approved
0.6759	Remote Similarity	NPD5248	Approved
0.6754	Remote Similarity	NPD8033	Approved
0.6754	Remote Similarity	NPD7503	Approved
0.6729	Remote Similarity	NPD5168	Approved
0.6729	Remote Similarity	NPD5128	Approved
0.6726	Remote Similarity	NPD7516	Approved
0.6703	Remote Similarity	NPD6118	Approved
0.6703	Remote Similarity	NPD6114	Approved
0.6703	Remote Similarity	NPD6115	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6697	Approved
0.6702	Remote Similarity	NPD4788	Approved
0.67	Remote Similarity	NPD7748	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6697	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD5215	Approved
0.6697	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5216	Approved
0.6697	Remote Similarity	NPD5127	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD8294	Approved
0.6609	Remote Similarity	NPD8296	Approved
0.6609	Remote Similarity	NPD8378	Approved
0.6609	Remote Similarity	NPD8380	Approved
0.6609	Remote Similarity	NPD8335	Approved
0.6609	Remote Similarity	NPD8379	Approved
0.66	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD5778	Approved
0.6559	Remote Similarity	NPD4821	Approved
0.6559	Remote Similarity	NPD4822	Approved
0.6559	Remote Similarity	NPD4819	Approved
0.6559	Remote Similarity	NPD4820	Approved
0.6552	Remote Similarity	NPD6370	Approved
0.6531	Remote Similarity	NPD4722	Approved
0.6531	Remote Similarity	NPD6672	Approved
0.6531	Remote Similarity	NPD4723	Approved
0.6531	Remote Similarity	NPD5737	Approved
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5362	Discontinued
0.6526	Remote Similarity	NPD5331	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6522	Remote Similarity	NPD6059	Approved
0.6522	Remote Similarity	NPD7741	Discontinued
0.6518	Remote Similarity	NPD5167	Approved

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