NPASS Compound

Structure

NPC185568 OpenBabel07101718292D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.0563 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4164 5.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 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 -3.9641 -2.8660 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7473 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 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 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2308 4.6974 0.0000 C 0 0 2 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 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5398 5.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 24 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 28 1 0 0 0 0 16 31 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 18 19 1 0 0 0 0 19 29 1 1 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 6 0 0 0 23 26 1 0 0 0 0 23 33 1 1 0 0 0 24 28 1 1 0 0 0 24 34 1 0 0 0 0 25 35 1 1 0 0 0 26 27 1 6 0 0 0 26 30 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	3.926
LogD:	3.652
LogS:	-3.927
# Rotatable Bonds:	6
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	5.448
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:	-5.065
MDCK Permeability:	4.923420419800095e-06
Pgp-inhibitor:	0.301
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.344
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	81.6723403930664%
Volume Distribution (VD):	0.737
Pgp-substrate:	10.566741943359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.315
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.861
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	4.289
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.265
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.339
Skin Sensitization:	0.221
Carcinogencity:	0.056
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC185568

Natural Product ID:	NPC185568
*Common Name:**	Balsaminapentaol A
IUPAC Name:	(3S,4S,7S,8R,9S,10S,13R,14S,17R)-17-[(2R,4R,5R)-4,5-dihydroxy-6-methylhept-6-en-2-yl]-4-(hydroxymethyl)-4,9,13,14-tetramethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Synonyms:
Standard InCHIKey:	LJWAEAIXBCCHLR-ITWKNSBQSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-17(2)25(35)22(32)14-18(3)19-10-11-30(7)26-23(33)15-21-20(8-9-24(34)28(21,5)16-31)27(26,4)12-13-29(19,30)6/h15,18-20,22-26,31-35H,1,8-14,16H2,2-7H3/t18-,19-,20-,22-,23+,24+,25-,26-,27+,28-,29-,30+/m1/s1
SMILES:	C=C(C)[C@H]([C@@H](C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3[C@H](C=C4[C@@H](CC[C@@H]([C@]4(C)CO)O)[C@]3(C)CC[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078341
PubChem CID:	44607275
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	=	47000.0	nM	PMID[556035]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	47000.0	nM	PMID[556036]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	33000.0	nM	PMID[556036]
NPT2	Others	Unspecified		Selectivity Index	=	3.2	n.a.	PMID[556036]
NPT2	Others	Unspecified		Selectivity Index	=	1.4	n.a.	PMID[556036]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	14600.0	nM	PMID[556036]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29300.0	nM	PMID[556037]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13700.0	nM	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	427.2	n.a.	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	429.0	n.a.	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	254.7	n.a.	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	252.0	n.a.	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	8.8	n.a.	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	38.2	n.a.	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.7	n.a.	PMID[556037]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	2.9	n.a.	PMID[556037]

☑ 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 NPC185568 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	163
0.1-0.2	1288
0.2-0.3	4850
0.3-0.4	14632
0.4-0.5	9272
0.5-0.6	5835
0.6-0.7	4822
0.7-0.8	1476
0.8-0.85	222
0.85-0.9	83
0.9-0.95	50
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC101462
0.962	High Similarity	NPC474634
0.95	High Similarity	NPC205845
0.9383	High Similarity	NPC266511
0.9375	High Similarity	NPC317458
0.9359	High Similarity	NPC84694
0.9359	High Similarity	NPC28862
0.9359	High Similarity	NPC109546
0.9359	High Similarity	NPC143182
0.9359	High Similarity	NPC47982
0.9359	High Similarity	NPC81306
0.9277	High Similarity	NPC67872
0.9268	High Similarity	NPC6391
0.925	High Similarity	NPC49964
0.925	High Similarity	NPC30166
0.9241	High Similarity	NPC234193
0.9231	High Similarity	NPC474216
0.9176	High Similarity	NPC97404
0.9176	High Similarity	NPC41554
0.9167	High Similarity	NPC470361
0.9157	High Similarity	NPC470620
0.9157	High Similarity	NPC149224
0.9125	High Similarity	NPC474531
0.9125	High Similarity	NPC264245
0.9125	High Similarity	NPC209620
0.9125	High Similarity	NPC23852
0.9114	High Similarity	NPC328714
0.9114	High Similarity	NPC30986
0.9114	High Similarity	NPC209430
0.9059	High Similarity	NPC329596
0.9059	High Similarity	NPC80561
0.9059	High Similarity	NPC204188
0.9059	High Similarity	NPC3345
0.9059	High Similarity	NPC291484
0.9059	High Similarity	NPC11216
0.9048	High Similarity	NPC474668
0.9036	High Similarity	NPC293287
0.9036	High Similarity	NPC152808
0.9036	High Similarity	NPC261266
0.9012	High Similarity	NPC50964
0.9012	High Similarity	NPC189972
0.9	High Similarity	NPC164840
0.9	High Similarity	NPC236112
0.9	High Similarity	NPC241290
0.9	High Similarity	NPC209944
0.8987	High Similarity	NPC83351
0.8987	High Similarity	NPC167891
0.8987	High Similarity	NPC473943
0.8974	High Similarity	NPC321381
0.8974	High Similarity	NPC107059
0.8974	High Similarity	NPC244488
0.8974	High Similarity	NPC240604
0.8974	High Similarity	NPC300324
0.8974	High Similarity	NPC321016
0.8974	High Similarity	NPC247325
0.8941	High Similarity	NPC477606
0.8916	High Similarity	NPC274448
0.8902	High Similarity	NPC475789
0.8889	High Similarity	NPC47761
0.8889	High Similarity	NPC470383
0.8889	High Similarity	NPC474759
0.8889	High Similarity	NPC474731
0.8889	High Similarity	NPC474683
0.8889	High Similarity	NPC82986
0.8889	High Similarity	NPC7505
0.8889	High Similarity	NPC474752
0.8861	High Similarity	NPC318495
0.8861	High Similarity	NPC198968
0.8861	High Similarity	NPC155986
0.8861	High Similarity	NPC477924
0.8846	High Similarity	NPC288035
0.8846	High Similarity	NPC304309
0.8846	High Similarity	NPC28657
0.8846	High Similarity	NPC162742
0.8846	High Similarity	NPC230301
0.8846	High Similarity	NPC22105
0.8846	High Similarity	NPC136188
0.8846	High Similarity	NPC285893
0.8846	High Similarity	NPC134847
0.8824	High Similarity	NPC133588
0.878	High Similarity	NPC470049
0.878	High Similarity	NPC87489
0.878	High Similarity	NPC296701
0.878	High Similarity	NPC218616
0.878	High Similarity	NPC202389
0.8765	High Similarity	NPC13554
0.8764	High Similarity	NPC288970
0.875	High Similarity	NPC477605
0.875	High Similarity	NPC477522
0.875	High Similarity	NPC87604
0.875	High Similarity	NPC275910
0.8734	High Similarity	NPC113733
0.8734	High Similarity	NPC189883
0.869	High Similarity	NPC318390
0.869	High Similarity	NPC157257
0.869	High Similarity	NPC470360
0.8675	High Similarity	NPC207013
0.8675	High Similarity	NPC470384
0.8642	High Similarity	NPC1319
0.8636	High Similarity	NPC310013
0.8625	High Similarity	NPC34019
0.8625	High Similarity	NPC214570
0.8625	High Similarity	NPC91594
0.8621	High Similarity	NPC295668
0.8608	High Similarity	NPC477923
0.8608	High Similarity	NPC141071
0.8608	High Similarity	NPC66566
0.8608	High Similarity	NPC257347
0.8608	High Similarity	NPC471723
0.8605	High Similarity	NPC280556
0.8588	High Similarity	NPC94462
0.8588	High Similarity	NPC125399
0.8588	High Similarity	NPC299068
0.8588	High Similarity	NPC477604
0.8571	High Similarity	NPC124172
0.8571	High Similarity	NPC474047
0.8571	High Similarity	NPC231310
0.8571	High Similarity	NPC238485
0.8571	High Similarity	NPC470077
0.8554	High Similarity	NPC470614
0.8554	High Similarity	NPC1272
0.8539	High Similarity	NPC65402
0.8539	High Similarity	NPC127718
0.8537	High Similarity	NPC102253
0.8537	High Similarity	NPC236237
0.8537	High Similarity	NPC22403
0.8537	High Similarity	NPC322313
0.8537	High Similarity	NPC26117
0.8523	High Similarity	NPC275671
0.8519	High Similarity	NPC6978
0.8519	High Similarity	NPC477514
0.8519	High Similarity	NPC244385
0.8519	High Similarity	NPC307965
0.8519	High Similarity	NPC285761
0.8519	High Similarity	NPC18603
0.8519	High Similarity	NPC76931
0.8519	High Similarity	NPC167037
0.8519	High Similarity	NPC138621
0.8506	High Similarity	NPC146554
0.8506	High Similarity	NPC32830
0.8506	High Similarity	NPC105495
0.85	High Similarity	NPC134330
0.85	High Similarity	NPC237460
0.85	High Similarity	NPC73875
0.85	High Similarity	NPC274079
0.85	High Similarity	NPC202642
0.85	High Similarity	NPC477925
0.85	High Similarity	NPC46160
0.85	High Similarity	NPC129165
0.85	High Similarity	NPC96319
0.8488	Intermediate Similarity	NPC475313
0.8481	Intermediate Similarity	NPC469533
0.8481	Intermediate Similarity	NPC469534
0.8481	Intermediate Similarity	NPC469593
0.8481	Intermediate Similarity	NPC471797
0.8462	Intermediate Similarity	NPC476893
0.8452	Intermediate Similarity	NPC82623
0.8452	Intermediate Similarity	NPC320548
0.8444	Intermediate Similarity	NPC8774
0.8444	Intermediate Similarity	NPC476894
0.8434	Intermediate Similarity	NPC476646
0.8434	Intermediate Similarity	NPC6707
0.8427	Intermediate Similarity	NPC307776
0.8415	Intermediate Similarity	NPC80530
0.8415	Intermediate Similarity	NPC273410
0.8409	Intermediate Similarity	NPC48010
0.8395	Intermediate Similarity	NPC470758
0.8395	Intermediate Similarity	NPC470711
0.8391	Intermediate Similarity	NPC471952
0.8391	Intermediate Similarity	NPC475664
0.8375	Intermediate Similarity	NPC185536
0.8375	Intermediate Similarity	NPC322353
0.8375	Intermediate Similarity	NPC121744
0.8375	Intermediate Similarity	NPC118508
0.8372	Intermediate Similarity	NPC269058
0.8372	Intermediate Similarity	NPC139724
0.8372	Intermediate Similarity	NPC24277
0.8372	Intermediate Similarity	NPC474970
0.8372	Intermediate Similarity	NPC71520
0.837	Intermediate Similarity	NPC476895
0.8354	Intermediate Similarity	NPC471799
0.8354	Intermediate Similarity	NPC474140
0.8353	Intermediate Similarity	NPC15534
0.8353	Intermediate Similarity	NPC478102
0.8353	Intermediate Similarity	NPC238992
0.8353	Intermediate Similarity	NPC209802
0.8352	Intermediate Similarity	NPC88009
0.8352	Intermediate Similarity	NPC227583
0.8352	Intermediate Similarity	NPC98457
0.8352	Intermediate Similarity	NPC12103
0.8352	Intermediate Similarity	NPC72204
0.8333	Intermediate Similarity	NPC248886
0.8333	Intermediate Similarity	NPC5985
0.8333	Intermediate Similarity	NPC47763
0.8333	Intermediate Similarity	NPC201852
0.8333	Intermediate Similarity	NPC7988
0.8333	Intermediate Similarity	NPC292793
0.8333	Intermediate Similarity	NPC34834
0.8315	Intermediate Similarity	NPC210268
0.8313	Intermediate Similarity	NPC295131

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 NPC185568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1498
0.2-0.3	4159
0.3-0.4	2316
0.4-0.5	581
0.5-0.6	173
0.6-0.7	182
0.7-0.8	76
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD6942	Approved
0.8846	High Similarity	NPD7339	Approved
0.8537	High Similarity	NPD7525	Registered
0.85	High Similarity	NPD3701	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6933	Approved
0.8193	Intermediate Similarity	NPD6929	Approved
0.814	Intermediate Similarity	NPD4786	Approved
0.8095	Intermediate Similarity	NPD6931	Approved
0.8095	Intermediate Similarity	NPD6930	Phase 2
0.8068	Intermediate Similarity	NPD7524	Approved
0.8025	Intermediate Similarity	NPD6924	Approved
0.8025	Intermediate Similarity	NPD6926	Approved
0.8023	Intermediate Similarity	NPD6695	Phase 3
0.7976	Intermediate Similarity	NPD7645	Phase 2
0.7952	Intermediate Similarity	NPD6925	Approved
0.7952	Intermediate Similarity	NPD5776	Phase 2
0.7931	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3667	Approved
0.7882	Intermediate Similarity	NPD7514	Phase 3
0.7857	Intermediate Similarity	NPD7145	Approved
0.7805	Intermediate Similarity	NPD4785	Approved
0.7805	Intermediate Similarity	NPD4784	Approved
0.7791	Intermediate Similarity	NPD6902	Approved
0.7778	Intermediate Similarity	NPD7150	Approved
0.7778	Intermediate Similarity	NPD7151	Approved
0.7778	Intermediate Similarity	NPD7152	Approved
0.7778	Intermediate Similarity	NPD4243	Approved
0.775	Intermediate Similarity	NPD6923	Approved
0.775	Intermediate Similarity	NPD6922	Approved
0.7692	Intermediate Similarity	NPD5328	Approved
0.7674	Intermediate Similarity	NPD7332	Phase 2
0.7667	Intermediate Similarity	NPD7750	Discontinued
0.7654	Intermediate Similarity	NPD7144	Approved
0.7654	Intermediate Similarity	NPD7143	Approved
0.7647	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6893	Approved
0.7556	Intermediate Similarity	NPD3618	Phase 1
0.7531	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6932	Approved
0.7527	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD8264	Approved
0.7471	Intermediate Similarity	NPD4748	Discontinued
0.7447	Intermediate Similarity	NPD6399	Phase 3
0.7386	Intermediate Similarity	NPD6898	Phase 1
0.7374	Intermediate Similarity	NPD5211	Phase 2
0.7356	Intermediate Similarity	NPD6683	Phase 2
0.7347	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.734	Intermediate Similarity	NPD7087	Discontinued
0.7333	Intermediate Similarity	NPD3668	Phase 3
0.7333	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7333	Intermediate Similarity	NPD3666	Approved
0.732	Intermediate Similarity	NPD4755	Approved
0.7312	Intermediate Similarity	NPD4753	Phase 2
0.7294	Intermediate Similarity	NPD4190	Phase 3
0.7294	Intermediate Similarity	NPD5275	Approved
0.729	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD7509	Discontinued
0.7263	Intermediate Similarity	NPD4202	Approved
0.7245	Intermediate Similarity	NPD7638	Approved
0.7245	Intermediate Similarity	NPD4225	Approved
0.7228	Intermediate Similarity	NPD5141	Approved
0.7216	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5221	Approved
0.7216	Intermediate Similarity	NPD4697	Phase 3
0.7216	Intermediate Similarity	NPD5222	Approved
0.7172	Intermediate Similarity	NPD4700	Approved
0.7172	Intermediate Similarity	NPD5286	Approved
0.7172	Intermediate Similarity	NPD4696	Approved
0.7172	Intermediate Similarity	NPD5285	Approved
0.7159	Intermediate Similarity	NPD4195	Approved
0.7158	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD5173	Approved
0.7128	Intermediate Similarity	NPD6051	Approved
0.71	Intermediate Similarity	NPD4159	Approved
0.7065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5224	Approved
0.703	Intermediate Similarity	NPD5226	Approved
0.703	Intermediate Similarity	NPD5225	Approved
0.703	Intermediate Similarity	NPD4633	Approved
0.699	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD5739	Approved
0.699	Remote Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD6675	Approved
0.6989	Remote Similarity	NPD5279	Phase 3
0.6979	Remote Similarity	NPD7515	Phase 2
0.697	Remote Similarity	NPD6084	Phase 2
0.697	Remote Similarity	NPD6083	Phase 2
0.6961	Remote Similarity	NPD5175	Approved
0.6961	Remote Similarity	NPD5174	Approved
0.6939	Remote Similarity	NPD4629	Approved
0.6939	Remote Similarity	NPD5210	Approved
0.6931	Remote Similarity	NPD5223	Approved
0.6923	Remote Similarity	NPD4221	Approved
0.6923	Remote Similarity	NPD4223	Phase 3
0.6887	Remote Similarity	NPD4634	Approved
0.6882	Remote Similarity	NPD5329	Approved
0.6875	Remote Similarity	NPD7136	Phase 2
0.6875	Remote Similarity	NPD368	Approved
0.6857	Remote Similarity	NPD7320	Approved
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6827	Remote Similarity	NPD4767	Approved
0.6827	Remote Similarity	NPD4768	Approved
0.6796	Remote Similarity	NPD4754	Approved
0.6792	Remote Similarity	NPD6373	Approved
0.6792	Remote Similarity	NPD6372	Approved
0.6774	Remote Similarity	NPD4197	Approved
0.6762	Remote Similarity	NPD6412	Phase 2
0.6762	Remote Similarity	NPD5701	Approved
0.6762	Remote Similarity	NPD5697	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6757	Remote Similarity	NPD7327	Approved
0.6757	Remote Similarity	NPD7328	Approved
0.6733	Remote Similarity	NPD5290	Discontinued
0.6729	Remote Similarity	NPD7102	Approved
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6726	Remote Similarity	NPD8033	Approved
0.6699	Remote Similarity	NPD7632	Discontinued
0.6698	Remote Similarity	NPD4730	Approved
0.6698	Remote Similarity	NPD4729	Approved
0.6698	Remote Similarity	NPD5128	Approved
0.6696	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6640	Phase 3
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6617	Approved
0.6637	Remote Similarity	NPD8377	Approved
0.6637	Remote Similarity	NPD8294	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6633	Remote Similarity	NPD8035	Phase 2
0.6633	Remote Similarity	NPD8034	Phase 2
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD4689	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.6632	Remote Similarity	NPD4138	Approved
0.6632	Remote Similarity	NPD5205	Approved
0.6632	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4693	Phase 3
0.6632	Remote Similarity	NPD6684	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD4688	Approved
0.6632	Remote Similarity	NPD4690	Approved
0.6632	Remote Similarity	NPD4623	Approved
0.6632	Remote Similarity	NPD4519	Discontinued
0.6632	Remote Similarity	NPD7334	Approved
0.6606	Remote Similarity	NPD6882	Approved
0.66	Remote Similarity	NPD5695	Phase 3
0.6579	Remote Similarity	NPD8379	Approved
0.6579	Remote Similarity	NPD8378	Approved
0.6579	Remote Similarity	NPD8296	Approved
0.6579	Remote Similarity	NPD8380	Approved
0.6579	Remote Similarity	NPD8335	Approved
0.6579	Remote Similarity	NPD7503	Approved
0.6574	Remote Similarity	NPD5250	Approved
0.6574	Remote Similarity	NPD5248	Approved
0.6574	Remote Similarity	NPD5251	Approved
0.6574	Remote Similarity	NPD5247	Approved
0.6574	Remote Similarity	NPD5249	Phase 3
0.6569	Remote Similarity	NPD5696	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6542	Remote Similarity	NPD5168	Approved
0.6542	Remote Similarity	NPD6011	Approved
0.6538	Remote Similarity	NPD342	Phase 1
0.6522	Remote Similarity	NPD4821	Approved
0.6522	Remote Similarity	NPD4819	Approved
0.6522	Remote Similarity	NPD4695	Discontinued
0.6522	Remote Similarity	NPD4822	Approved
0.6522	Remote Similarity	NPD4820	Approved
0.6514	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5215	Approved
0.6514	Remote Similarity	NPD5217	Approved
0.6514	Remote Similarity	NPD5216	Approved
0.6495	Remote Similarity	NPD6903	Approved
0.6495	Remote Similarity	NPD4723	Approved
0.6495	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4722	Approved
0.6489	Remote Similarity	NPD5362	Discontinued
0.6489	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD5331	Approved
0.6484	Remote Similarity	NPD4271	Approved
0.6484	Remote Similarity	NPD4268	Approved
0.6484	Remote Similarity	NPD3617	Approved
0.6471	Remote Similarity	NPD7902	Approved
0.6458	Remote Similarity	NPD5280	Approved
0.6458	Remote Similarity	NPD5690	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