NPASS Compound

Structure

NPC473527 OpenBabel07101718182D 44 47 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 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 -2.5075 -2.3901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 -2.8783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3944 4.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8944 4.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6153 3.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5462 4.2107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 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 -3.1055 1.7930 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 2.9577 2.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6629 1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9716 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2538 -1.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2819 -0.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5357 -2.1545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8944 4.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3944 3.1472 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.9716 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1055 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 1.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3972 3.2219 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 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.8376 -0.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1055 -1.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 2.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0196 2.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4959 0.1590 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 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 2 0 0 0 0 6 23 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 38 1 0 0 0 0 19 24 2 0 0 0 0 19 29 1 0 0 0 0 20 35 1 0 0 0 0 20 37 1 0 0 0 0 23 25 1 0 0 0 0 24 31 1 0 0 0 0 25 35 1 0 0 0 0 26 27 1 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 28 29 2 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 31 1 0 0 0 0 30 32 2 0 0 0 0 30 33 1 0 0 0 0 31 41 2 0 0 0 0 32 37 1 0 0 0 0 32 42 1 0 0 0 0 33 38 1 0 0 0 0 33 43 2 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 36 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.36
Volume:	657.955
LogP:	7.77
LogD:	5.13
LogS:	-3.735
# Rotatable Bonds:	7
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	6.352
Fsp3:	0.579
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.15
MDCK Permeability:	1.6168640286196023e-05
Pgp-inhibitor:	0.065
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.341
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.731

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	99.3217544555664%
Volume Distribution (VD):	2.257
Pgp-substrate:	1.2497550249099731%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.698
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.557
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.879

ADMET: Excretion

Clearance (CL):	18.623
Half-life (T1/2):	0.025

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.203
Skin Sensitization:	0.004
Carcinogencity:	0.215
Eye Corrosion:	0.006
Eye Irritation:	0.247
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC473527

Natural Product ID:	NPC473527
*Common Name:**	Guttiferone H
IUPAC Name:	n.a.
Synonyms:	Guttiferone H
Standard InCHIKey:	IIOQLCJBRQEPIR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C38H50O6/c1-21(2)11-13-26-27-15-14-25(23(5)6)35(7,8)20-37(27)32(42)30(31(41)24-12-16-28(39)29(40)19-24)33(43)38(34(37)44,36(26,9)10)18-17-22(3)4/h11-12,16-17,19,25-27,39-40,42H,5,13-15,18,20H2,1-4,6-10H3
SMILES:	CC(=CCC12C(=O)C(=C(C3(C1=O)CC(C)(C)C(CCC3C(C2(C)C)CC=C(C)C)C(=C)C)O)C(=O)c1ccc(c(c1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444720
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14600386]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[15787435]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	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
Others	5

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	12400.0	nM	PMID[544682]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	11.8	%	PMID[544682]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	15.6	%	PMID[544682]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	19.8	%	PMID[544682]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	48.0	%	PMID[544682]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	80.0	%	PMID[544682]
NPT1	Others	Radical scavenging activity		IC50	=	64000.0	nM	PMID[544682]

☑ 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 NPC473527 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	385
0.1-0.2	1564
0.2-0.3	3214
0.3-0.4	8405
0.4-0.5	10900
0.5-0.6	6888
0.6-0.7	9855
0.7-0.8	1378
0.8-0.85	47
0.85-0.9	13
0.9-0.95	24
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC245760
0.985	High Similarity	NPC165191
0.985	High Similarity	NPC5014
0.985	High Similarity	NPC42384
0.985	High Similarity	NPC28592
0.985	High Similarity	NPC149773
0.985	High Similarity	NPC114333
0.985	High Similarity	NPC289358
0.985	High Similarity	NPC46242
0.985	High Similarity	NPC297797
0.985	High Similarity	NPC91887
0.985	High Similarity	NPC23667
0.985	High Similarity	NPC469857
0.985	High Similarity	NPC51531
0.985	High Similarity	NPC477849
0.985	High Similarity	NPC473479
0.985	High Similarity	NPC157284
0.985	High Similarity	NPC473779
0.985	High Similarity	NPC50615
0.9776	High Similarity	NPC294330
0.9699	High Similarity	NPC7464
0.9562	High Similarity	NPC471971
0.9562	High Similarity	NPC30846
0.9562	High Similarity	NPC469855
0.9562	High Similarity	NPC471972
0.9424	High Similarity	NPC145301
0.9424	High Similarity	NPC294679
0.9424	High Similarity	NPC469856
0.9424	High Similarity	NPC144247
0.9424	High Similarity	NPC469375
0.9424	High Similarity	NPC8493
0.9424	High Similarity	NPC469854
0.9412	High Similarity	NPC471974
0.9412	High Similarity	NPC469681
0.9412	High Similarity	NPC469680
0.9291	High Similarity	NPC471970
0.9173	High Similarity	NPC25736
0.9161	High Similarity	NPC264229
0.9161	High Similarity	NPC132810
0.9161	High Similarity	NPC46549
0.9097	High Similarity	NPC237441
0.9044	High Similarity	NPC474715
0.9021	High Similarity	NPC273798
0.8904	High Similarity	NPC48949
0.8851	High Similarity	NPC305710
0.8768	High Similarity	NPC4170
0.8768	High Similarity	NPC138472
0.8652	High Similarity	NPC118366
0.8652	High Similarity	NPC277559
0.8633	High Similarity	NPC111845
0.8592	High Similarity	NPC230811
0.8551	High Similarity	NPC117609
0.854	High Similarity	NPC234175
0.8521	High Similarity	NPC49911
0.8511	High Similarity	NPC43353
0.8511	High Similarity	NPC153088
0.85	High Similarity	NPC294226
0.8487	Intermediate Similarity	NPC471968
0.8472	Intermediate Similarity	NPC470035
0.8435	Intermediate Similarity	NPC470038
0.8425	Intermediate Similarity	NPC199936
0.838	Intermediate Similarity	NPC258502
0.8356	Intermediate Similarity	NPC184935
0.8345	Intermediate Similarity	NPC471853
0.8345	Intermediate Similarity	NPC476534
0.8333	Intermediate Similarity	NPC416
0.8333	Intermediate Similarity	NPC72667
0.8333	Intermediate Similarity	NPC61398
0.8322	Intermediate Similarity	NPC10842
0.8311	Intermediate Similarity	NPC258856
0.8264	Intermediate Similarity	NPC471152
0.8261	Intermediate Similarity	NPC254492
0.8261	Intermediate Similarity	NPC15837
0.8252	Intermediate Similarity	NPC72918
0.8231	Intermediate Similarity	NPC291078
0.8231	Intermediate Similarity	NPC176030
0.8231	Intermediate Similarity	NPC248068
0.8231	Intermediate Similarity	NPC192597
0.8231	Intermediate Similarity	NPC169214
0.8231	Intermediate Similarity	NPC229218
0.8231	Intermediate Similarity	NPC141817
0.8214	Intermediate Similarity	NPC171460
0.8201	Intermediate Similarity	NPC78364
0.8201	Intermediate Similarity	NPC84672
0.8201	Intermediate Similarity	NPC324209
0.8201	Intermediate Similarity	NPC69424
0.8201	Intermediate Similarity	NPC176130
0.82	Intermediate Similarity	NPC52692
0.8195	Intermediate Similarity	NPC150919
0.8194	Intermediate Similarity	NPC474311
0.8188	Intermediate Similarity	NPC75295
0.8158	Intermediate Similarity	NPC470037
0.8156	Intermediate Similarity	NPC108129
0.8151	Intermediate Similarity	NPC472903
0.8143	Intermediate Similarity	NPC96024
0.8138	Intermediate Similarity	NPC290030
0.8138	Intermediate Similarity	NPC147418
0.8138	Intermediate Similarity	NPC264022
0.8138	Intermediate Similarity	NPC475957
0.8125	Intermediate Similarity	NPC478060
0.8125	Intermediate Similarity	NPC471975
0.8125	Intermediate Similarity	NPC470374
0.8125	Intermediate Similarity	NPC478059
0.8125	Intermediate Similarity	NPC470377
0.8116	Intermediate Similarity	NPC199273
0.8116	Intermediate Similarity	NPC15127
0.8112	Intermediate Similarity	NPC477139
0.8112	Intermediate Similarity	NPC53896
0.8102	Intermediate Similarity	NPC91478
0.8095	Intermediate Similarity	NPC203063
0.8088	Intermediate Similarity	NPC236520
0.8088	Intermediate Similarity	NPC294361
0.8085	Intermediate Similarity	NPC276238
0.8085	Intermediate Similarity	NPC117899
0.8082	Intermediate Similarity	NPC87723
0.8071	Intermediate Similarity	NPC471530
0.8069	Intermediate Similarity	NPC65005
0.8069	Intermediate Similarity	NPC194764
0.8069	Intermediate Similarity	NPC193358
0.8069	Intermediate Similarity	NPC264112
0.8056	Intermediate Similarity	NPC202225
0.8056	Intermediate Similarity	NPC50924
0.8054	Intermediate Similarity	NPC224884
0.8054	Intermediate Similarity	NPC209085
0.8041	Intermediate Similarity	NPC472904
0.8029	Intermediate Similarity	NPC120545
0.8014	Intermediate Similarity	NPC53001
0.8014	Intermediate Similarity	NPC193203
0.8013	Intermediate Similarity	NPC143685
0.8	Intermediate Similarity	NPC80035
0.8	Intermediate Similarity	NPC3224
0.8	Intermediate Similarity	NPC71610
0.8	Intermediate Similarity	NPC196941
0.8	Intermediate Similarity	NPC309169
0.7987	Intermediate Similarity	NPC144283
0.7987	Intermediate Similarity	NPC477873
0.7987	Intermediate Similarity	NPC469447
0.7987	Intermediate Similarity	NPC35
0.7987	Intermediate Similarity	NPC193555
0.7986	Intermediate Similarity	NPC115458
0.7985	Intermediate Similarity	NPC277394
0.7985	Intermediate Similarity	NPC61062
0.7985	Intermediate Similarity	NPC299252
0.7972	Intermediate Similarity	NPC18798
0.7972	Intermediate Similarity	NPC17083
0.7972	Intermediate Similarity	NPC471851
0.7972	Intermediate Similarity	NPC244699
0.7972	Intermediate Similarity	NPC291001
0.7971	Intermediate Similarity	NPC282577
0.7971	Intermediate Similarity	NPC86900
0.7959	Intermediate Similarity	NPC206207
0.7959	Intermediate Similarity	NPC4214
0.7959	Intermediate Similarity	NPC13715
0.7958	Intermediate Similarity	NPC303910
0.7947	Intermediate Similarity	NPC73416
0.7947	Intermediate Similarity	NPC160777
0.7945	Intermediate Similarity	NPC472308
0.7943	Intermediate Similarity	NPC107672
0.7933	Intermediate Similarity	NPC238629
0.7933	Intermediate Similarity	NPC239608
0.7933	Intermediate Similarity	NPC46161
0.7931	Intermediate Similarity	NPC293454
0.7931	Intermediate Similarity	NPC475088
0.7927	Intermediate Similarity	NPC471969
0.7919	Intermediate Similarity	NPC472410
0.7919	Intermediate Similarity	NPC84273
0.7917	Intermediate Similarity	NPC135801
0.7917	Intermediate Similarity	NPC175738
0.791	Intermediate Similarity	NPC322197
0.7899	Intermediate Similarity	NPC154696
0.7895	Intermediate Similarity	NPC234637
0.7895	Intermediate Similarity	NPC130591
0.7895	Intermediate Similarity	NPC476535
0.7891	Intermediate Similarity	NPC36868
0.7887	Intermediate Similarity	NPC3009
0.7887	Intermediate Similarity	NPC229894
0.7887	Intermediate Similarity	NPC48248
0.7881	Intermediate Similarity	NPC79627
0.7881	Intermediate Similarity	NPC53520
0.7877	Intermediate Similarity	NPC249272
0.7877	Intermediate Similarity	NPC477596
0.7877	Intermediate Similarity	NPC283088
0.7872	Intermediate Similarity	NPC306765
0.7871	Intermediate Similarity	NPC124842
0.7867	Intermediate Similarity	NPC11314
0.7862	Intermediate Similarity	NPC78307
0.7862	Intermediate Similarity	NPC327410
0.7857	Intermediate Similarity	NPC142654
0.7852	Intermediate Similarity	NPC181560
0.7852	Intermediate Similarity	NPC169452
0.7847	Intermediate Similarity	NPC469526
0.7847	Intermediate Similarity	NPC243305
0.7847	Intermediate Similarity	NPC34070
0.7843	Intermediate Similarity	NPC476821
0.7842	Intermediate Similarity	NPC139171
0.7842	Intermediate Similarity	NPC68167
0.7838	Intermediate Similarity	NPC141368
0.7838	Intermediate Similarity	NPC473622
0.7834	Intermediate Similarity	NPC472807
0.7832	Intermediate Similarity	NPC34414

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 NPC473527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	943
0.2-0.3	1496
0.3-0.4	2900
0.4-0.5	2153
0.5-0.6	992
0.6-0.7	293
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8163	Intermediate Similarity	NPD8166	Discontinued
0.7917	Intermediate Similarity	NPD943	Approved
0.7883	Intermediate Similarity	NPD2932	Approved
0.7754	Intermediate Similarity	NPD3019	Approved
0.7703	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1470	Approved
0.7597	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1201	Approved
0.7468	Intermediate Similarity	NPD3300	Phase 2
0.7464	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3022	Approved
0.7463	Intermediate Similarity	NPD3021	Approved
0.7429	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3023	Approved
0.7324	Intermediate Similarity	NPD3026	Approved
0.7305	Intermediate Similarity	NPD3024	Approved
0.7305	Intermediate Similarity	NPD3025	Approved
0.7222	Intermediate Similarity	NPD9269	Phase 2
0.7222	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9494	Approved
0.7202	Intermediate Similarity	NPD7473	Discontinued
0.7197	Intermediate Similarity	NPD7390	Discontinued
0.719	Intermediate Similarity	NPD5405	Approved
0.719	Intermediate Similarity	NPD5406	Approved
0.719	Intermediate Similarity	NPD5408	Approved
0.719	Intermediate Similarity	NPD5404	Approved
0.7172	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6663	Approved
0.7124	Intermediate Similarity	NPD2799	Discontinued
0.7117	Intermediate Similarity	NPD2801	Approved
0.7095	Intermediate Similarity	NPD5736	Approved
0.7089	Intermediate Similarity	NPD1511	Approved
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7055	Intermediate Similarity	NPD1934	Approved
0.7039	Intermediate Similarity	NPD230	Phase 1
0.7032	Intermediate Similarity	NPD2344	Approved
0.703	Intermediate Similarity	NPD3882	Suspended
0.7024	Intermediate Similarity	NPD6232	Discontinued
0.7007	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1512	Approved
0.6975	Remote Similarity	NPD3226	Approved
0.697	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2935	Discontinued
0.6959	Remote Similarity	NPD1164	Approved
0.6954	Remote Similarity	NPD3764	Approved
0.695	Remote Similarity	NPD5951	Approved
0.6944	Remote Similarity	NPD9268	Approved
0.6933	Remote Similarity	NPD7028	Phase 2
0.6932	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD1471	Phase 3
0.6918	Remote Similarity	NPD3092	Approved
0.6913	Remote Similarity	NPD2798	Approved
0.6909	Remote Similarity	NPD7819	Suspended
0.6899	Remote Similarity	NPD7003	Approved
0.6893	Remote Similarity	NPD8434	Phase 2
0.6875	Remote Similarity	NPD3091	Approved
0.6855	Remote Similarity	NPD2309	Approved
0.6855	Remote Similarity	NPD6190	Approved
0.6846	Remote Similarity	NPD3094	Phase 2
0.6835	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1755	Approved
0.6818	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8150	Discontinued
0.6797	Remote Similarity	NPD8032	Phase 2
0.6795	Remote Similarity	NPD1510	Phase 2
0.6791	Remote Similarity	NPD3020	Approved
0.679	Remote Similarity	NPD6273	Approved
0.6781	Remote Similarity	NPD4059	Approved
0.6781	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1876	Approved
0.6774	Remote Similarity	NPD6651	Approved
0.6774	Remote Similarity	NPD1607	Approved
0.6763	Remote Similarity	NPD3818	Discontinued
0.6757	Remote Similarity	NPD4878	Approved
0.6753	Remote Similarity	NPD3620	Phase 2
0.6753	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1240	Approved
0.6752	Remote Similarity	NPD6099	Approved
0.6752	Remote Similarity	NPD6100	Approved
0.675	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6166	Phase 2
0.6744	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2800	Approved
0.6728	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4380	Phase 2
0.6726	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5494	Approved
0.669	Remote Similarity	NPD5536	Phase 2
0.669	Remote Similarity	NPD7610	Discontinued
0.6689	Remote Similarity	NPD258	Approved
0.6689	Remote Similarity	NPD257	Approved
0.6687	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7075	Discontinued
0.6686	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD9545	Approved
0.6629	Remote Similarity	NPD7054	Approved
0.6627	Remote Similarity	NPD6599	Discontinued
0.6626	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3268	Approved
0.6623	Remote Similarity	NPD2313	Discontinued
0.662	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7685	Pre-registration
0.661	Remote Similarity	NPD5027	Approved
0.661	Remote Similarity	NPD5031	Approved
0.661	Remote Similarity	NPD5029	Approved
0.6607	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1465	Phase 2
0.6605	Remote Similarity	NPD7236	Approved
0.6603	Remote Similarity	NPD447	Suspended
0.6599	Remote Similarity	NPD1651	Approved
0.6591	Remote Similarity	NPD7472	Approved
0.6587	Remote Similarity	NPD7411	Suspended
0.6587	Remote Similarity	NPD6873	Phase 2
0.6584	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3750	Approved
0.6584	Remote Similarity	NPD4110	Phase 3
0.6573	Remote Similarity	NPD4954	Approved
0.6573	Remote Similarity	NPD36	Approved
0.6573	Remote Similarity	NPD7635	Approved
0.6573	Remote Similarity	NPD5032	Approved
0.6573	Remote Similarity	NPD4955	Approved
0.6573	Remote Similarity	NPD5026	Approved
0.6573	Remote Similarity	NPD5028	Approved
0.6573	Remote Similarity	NPD5034	Approved
0.6568	Remote Similarity	NPD5977	Approved
0.6568	Remote Similarity	NPD3817	Phase 2
0.6568	Remote Similarity	NPD5978	Approved
0.6567	Remote Similarity	NPD2859	Approved
0.6567	Remote Similarity	NPD2860	Approved
0.6562	Remote Similarity	NPD1549	Phase 2
0.6558	Remote Similarity	NPD7095	Approved
0.6558	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1751	Approved
0.6554	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD826	Approved
0.6538	Remote Similarity	NPD825	Approved
0.6536	Remote Similarity	NPD5035	Approved
0.6534	Remote Similarity	NPD5844	Phase 1
0.6525	Remote Similarity	NPD74	Approved
0.6525	Remote Similarity	NPD9266	Approved
0.6524	Remote Similarity	NPD2532	Approved
0.6524	Remote Similarity	NPD2534	Approved
0.6524	Remote Similarity	NPD2533	Approved
0.6522	Remote Similarity	NPD1930	Approved
0.6522	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1929	Approved
0.6517	Remote Similarity	NPD7251	Discontinued
0.6517	Remote Similarity	NPD5030	Phase 2
0.6507	Remote Similarity	NPD9493	Approved
0.65	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7266	Discontinued
0.65	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2934	Approved
0.6493	Remote Similarity	NPD2933	Approved
0.6489	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2629	Approved
0.648	Remote Similarity	NPD7808	Phase 3
0.6474	Remote Similarity	NPD6959	Discontinued
0.6467	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1281	Approved
0.6461	Remote Similarity	NPD6797	Phase 2
0.6454	Remote Similarity	NPD9263	Approved
0.6454	Remote Similarity	NPD9264	Approved
0.6454	Remote Similarity	NPD9267	Approved
0.6453	Remote Similarity	NPD6234	Discontinued
0.6448	Remote Similarity	NPD6836	Approved
0.6444	Remote Similarity	NPD8312	Approved
0.6444	Remote Similarity	NPD8313	Approved
0.6441	Remote Similarity	NPD1221	Approved
0.6438	Remote Similarity	NPD2796	Approved
0.6433	Remote Similarity	NPD7768	Phase 2
0.6429	Remote Similarity	NPD9569	Approved
0.6429	Remote Similarity	NPD5038	Approved
0.6429	Remote Similarity	NPD5037	Approved
0.6424	Remote Similarity	NPD1608	Approved
0.6423	Remote Similarity	NPD2066	Phase 3
0.6419	Remote Similarity	NPD7009	Phase 2
0.6414	Remote Similarity	NPD5283	Phase 1
0.6412	Remote Similarity	NPD5760	Phase 2
0.6412	Remote Similarity	NPD5761	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