NPASS Compound

Structure

NPC23667 OpenBabel07101718272D 49 51 0 0 1 0 0 0 0 0999 V2000 -6.7926 4.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9435 6.3728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6020 3.0374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1314 3.8865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7655 -3.6383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1733 -4.2285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6146 2.1676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8996 0.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0944 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3589 1.3393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0944 3.9217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8491 2.1884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0944 4.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1314 2.1884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2454 3.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3963 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0447 -1.1834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3963 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8938 -1.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4582 -2.5544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3073 1.0838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3393 1.3393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5083 -2.3899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9665 0.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8938 0.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9435 5.3923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6216 3.0374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7990 -3.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2738 1.2483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2454 2.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0447 -0.2030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7429 -1.1834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7429 -0.2030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3466 -0.2030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1957 0.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4031 -0.9566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7222 0.2228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8491 0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8491 -1.4706 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 -5.5920 -1.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5920 0.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1957 1.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3157 -1.3148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8683 1.1922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8491 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 30 1 0 0 0 0 9 31 1 0 0 0 0 10 41 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 27 2 0 0 0 0 14 28 2 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 16 31 2 0 0 0 0 17 19 2 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 23 1 0 0 0 0 20 29 2 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 41 1 0 0 0 0 25 32 2 0 0 0 0 25 35 1 0 0 0 0 26 33 1 0 0 0 0 26 42 1 0 0 0 0 32 37 1 0 0 0 0 33 41 1 6 0 0 0 34 35 2 0 0 0 0 34 44 1 0 0 0 0 35 45 1 0 0 0 0 36 37 1 0 0 0 0 36 38 2 0 0 0 0 36 39 1 0 0 0 0 37 46 2 0 0 0 0 38 42 1 0 0 0 0 38 47 1 0 0 0 0 39 43 1 0 0 0 0 39 48 2 0 0 0 0 40 42 1 0 0 0 0 40 43 1 0 0 0 0 40 49 2 0 0 0 0 41 43 1 1 0 0 0 42 23 1 6 0 0 0 43 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	670.42
Volume:	747.718
LogP:	9.402
LogD:	6.403
LogS:	-3.945
# Rotatable Bonds:	14
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.088
Synthetic Accessibility Score:	5.866
Fsp3:	0.535
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:	-5.105
MDCK Permeability:	1.8931103113573045e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.207
Human Intestinal Absorption (HIA):	0.3
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	98.20136260986328%
Volume Distribution (VD):	2.626
Pgp-substrate:	7.364878177642822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.688
CYP2C19-substrate:	0.393
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.783
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.801
CYP3A4-substrate:	0.694

ADMET: Excretion

Clearance (CL):	14.299
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.819
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.047
Carcinogencity:	0.301
Eye Corrosion:	0.01
Eye Irritation:	0.242
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC23667

Natural Product ID:	NPC23667
*Common Name:**	Guttiferone I
IUPAC Name:	n.a.
Synonyms:	Guttiferone I
Standard InCHIKey:	XIKKSUTXFFVDEF-VOWDTJCUSA-N
Standard InCHI:	InChI=1S/C43H58O6/c1-27(2)13-11-15-31(9)16-18-33-26-42(23-20-29(5)6)38(47)36(37(46)32-17-19-34(44)35(45)25-32)39(48)43(40(42)49,24-21-30(7)8)41(33,10)22-12-14-28(3)4/h13-14,16-17,19-21,25,33,44-45,47H,11-12,15,18,22-24,26H2,1-10H3/b31-16+/t33-,41+,42-,43+/m0/s1
SMILES:	CC(=CCC/C(=C/C[C@H]1C[C@@]2(CC=C(C)C)C(=C(C(=O)c3ccc(c(c3)O)O)C(=O)[C@](CC=C(C)C)(C2=O)[C@]1(C)CCC=C(C)C)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445689
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO26536	Garcinia humilis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844964]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20594858]
NPO26536	Garcinia humilis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15264	Garcinia paucinervis	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	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	IC50	=	3400.0	nM	PMID[549949]
NPT1746	Individual Protein	LXR-beta	Homo sapiens	IC50	>	15000.0	nM	PMID[549949]
NPT6536	Others	Liver X receptor (LXR alpha AND LXR beta)	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[549949]

☑ 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 NPC23667 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	358
0.1-0.2	1496
0.2-0.3	3022
0.3-0.4	7831
0.4-0.5	10973
0.5-0.6	6501
0.6-0.7	9938
0.7-0.8	2417
0.8-0.85	90
0.85-0.9	16
0.9-0.95	20
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289358
1.0	High Similarity	NPC165191
1.0	High Similarity	NPC5014
1.0	High Similarity	NPC51531
1.0	High Similarity	NPC469857
1.0	High Similarity	NPC114333
1.0	High Similarity	NPC297797
1.0	High Similarity	NPC91887
1.0	High Similarity	NPC157284
1.0	High Similarity	NPC245760
1.0	High Similarity	NPC50615
1.0	High Similarity	NPC473779
1.0	High Similarity	NPC473479
1.0	High Similarity	NPC28592
1.0	High Similarity	NPC149773
1.0	High Similarity	NPC46242
1.0	High Similarity	NPC477849
1.0	High Similarity	NPC42384
0.9924	High Similarity	NPC294330
0.985	High Similarity	NPC473527
0.9847	High Similarity	NPC7464
0.9704	High Similarity	NPC471972
0.9704	High Similarity	NPC469855
0.9704	High Similarity	NPC471971
0.9704	High Similarity	NPC30846
0.9562	High Similarity	NPC294679
0.9562	High Similarity	NPC8493
0.9562	High Similarity	NPC469854
0.9562	High Similarity	NPC469856
0.9562	High Similarity	NPC145301
0.9562	High Similarity	NPC469375
0.9562	High Similarity	NPC144247
0.9552	High Similarity	NPC469680
0.9552	High Similarity	NPC469681
0.9552	High Similarity	NPC471974
0.9424	High Similarity	NPC471970
0.9313	High Similarity	NPC25736
0.9291	High Similarity	NPC46549
0.9291	High Similarity	NPC264229
0.9291	High Similarity	NPC132810
0.9225	High Similarity	NPC237441
0.9149	High Similarity	NPC273798
0.9028	High Similarity	NPC48949
0.8973	High Similarity	NPC305710
0.8897	High Similarity	NPC138472
0.8897	High Similarity	NPC4170
0.8897	High Similarity	NPC474715
0.8777	High Similarity	NPC118366
0.8777	High Similarity	NPC277559
0.8759	High Similarity	NPC111845
0.8714	High Similarity	NPC230811
0.8676	High Similarity	NPC117609
0.8667	High Similarity	NPC234175
0.8643	High Similarity	NPC49911
0.8633	High Similarity	NPC153088
0.8633	High Similarity	NPC43353
0.8623	High Similarity	NPC294226
0.86	High Similarity	NPC471968
0.8592	High Similarity	NPC470035
0.8552	High Similarity	NPC470038
0.8542	High Similarity	NPC199936
0.85	High Similarity	NPC258502
0.8472	Intermediate Similarity	NPC184935
0.8462	Intermediate Similarity	NPC471853
0.8462	Intermediate Similarity	NPC476534
0.8456	Intermediate Similarity	NPC72667
0.8451	Intermediate Similarity	NPC61398
0.8451	Intermediate Similarity	NPC416
0.8435	Intermediate Similarity	NPC10842
0.8425	Intermediate Similarity	NPC258856
0.8382	Intermediate Similarity	NPC254492
0.8382	Intermediate Similarity	NPC15837
0.838	Intermediate Similarity	NPC471152
0.8369	Intermediate Similarity	NPC72918
0.8345	Intermediate Similarity	NPC141817
0.8345	Intermediate Similarity	NPC176030
0.8345	Intermediate Similarity	NPC229218
0.8345	Intermediate Similarity	NPC192597
0.8345	Intermediate Similarity	NPC291078
0.8345	Intermediate Similarity	NPC248068
0.8345	Intermediate Similarity	NPC169214
0.8333	Intermediate Similarity	NPC171460
0.8321	Intermediate Similarity	NPC84672
0.8321	Intermediate Similarity	NPC69424
0.8321	Intermediate Similarity	NPC176130
0.8321	Intermediate Similarity	NPC324209
0.8321	Intermediate Similarity	NPC150919
0.8321	Intermediate Similarity	NPC78364
0.8311	Intermediate Similarity	NPC52692
0.831	Intermediate Similarity	NPC474311
0.8299	Intermediate Similarity	NPC75295
0.8273	Intermediate Similarity	NPC108129
0.8267	Intermediate Similarity	NPC470037
0.8264	Intermediate Similarity	NPC472903
0.8261	Intermediate Similarity	NPC96024
0.8252	Intermediate Similarity	NPC290030
0.8252	Intermediate Similarity	NPC475957
0.8252	Intermediate Similarity	NPC147418
0.8252	Intermediate Similarity	NPC264022
0.8235	Intermediate Similarity	NPC199273
0.8235	Intermediate Similarity	NPC15127
0.8228	Intermediate Similarity	NPC478060
0.8228	Intermediate Similarity	NPC471975
0.8228	Intermediate Similarity	NPC470374
0.8228	Intermediate Similarity	NPC478059
0.8228	Intermediate Similarity	NPC470377
0.8227	Intermediate Similarity	NPC477139
0.8227	Intermediate Similarity	NPC53896
0.8222	Intermediate Similarity	NPC91478
0.8209	Intermediate Similarity	NPC236520
0.8209	Intermediate Similarity	NPC294361
0.8207	Intermediate Similarity	NPC203063
0.8201	Intermediate Similarity	NPC117899
0.8201	Intermediate Similarity	NPC276238
0.8194	Intermediate Similarity	NPC87723
0.8188	Intermediate Similarity	NPC471530
0.8182	Intermediate Similarity	NPC193358
0.8182	Intermediate Similarity	NPC264112
0.8182	Intermediate Similarity	NPC194764
0.8182	Intermediate Similarity	NPC65005
0.8169	Intermediate Similarity	NPC50924
0.8169	Intermediate Similarity	NPC202225
0.8163	Intermediate Similarity	NPC209085
0.8163	Intermediate Similarity	NPC224884
0.8151	Intermediate Similarity	NPC472904
0.8148	Intermediate Similarity	NPC120545
0.8129	Intermediate Similarity	NPC193203
0.8125	Intermediate Similarity	NPC53001
0.8121	Intermediate Similarity	NPC143685
0.8116	Intermediate Similarity	NPC71610
0.8116	Intermediate Similarity	NPC3224
0.8112	Intermediate Similarity	NPC80035
0.8108	Intermediate Similarity	NPC309169
0.8108	Intermediate Similarity	NPC196941
0.8106	Intermediate Similarity	NPC277394
0.8106	Intermediate Similarity	NPC61062
0.8106	Intermediate Similarity	NPC299252
0.8099	Intermediate Similarity	NPC115458
0.8095	Intermediate Similarity	NPC477873
0.8095	Intermediate Similarity	NPC469447
0.8095	Intermediate Similarity	NPC193555
0.8092	Intermediate Similarity	NPC144283
0.8092	Intermediate Similarity	NPC35
0.8088	Intermediate Similarity	NPC86900
0.8088	Intermediate Similarity	NPC282577
0.8085	Intermediate Similarity	NPC244699
0.8085	Intermediate Similarity	NPC471851
0.8085	Intermediate Similarity	NPC17083
0.8085	Intermediate Similarity	NPC18798
0.8085	Intermediate Similarity	NPC291001
0.8071	Intermediate Similarity	NPC303910
0.8069	Intermediate Similarity	NPC13715
0.8069	Intermediate Similarity	NPC4214
0.8069	Intermediate Similarity	NPC206207
0.8058	Intermediate Similarity	NPC107672
0.8056	Intermediate Similarity	NPC472308
0.8054	Intermediate Similarity	NPC160777
0.8054	Intermediate Similarity	NPC73416
0.8042	Intermediate Similarity	NPC475088
0.8042	Intermediate Similarity	NPC293454
0.8041	Intermediate Similarity	NPC239608
0.8041	Intermediate Similarity	NPC46161
0.8041	Intermediate Similarity	NPC238629
0.803	Intermediate Similarity	NPC322197
0.8028	Intermediate Similarity	NPC175738
0.8028	Intermediate Similarity	NPC135801
0.8027	Intermediate Similarity	NPC84273
0.8027	Intermediate Similarity	NPC472410
0.8025	Intermediate Similarity	NPC471969
0.8015	Intermediate Similarity	NPC130591
0.8015	Intermediate Similarity	NPC234637
0.8015	Intermediate Similarity	NPC154696
0.8	Intermediate Similarity	NPC476535
0.8	Intermediate Similarity	NPC3009
0.8	Intermediate Similarity	NPC36868
0.8	Intermediate Similarity	NPC229894
0.8	Intermediate Similarity	NPC48248
0.7987	Intermediate Similarity	NPC79627
0.7987	Intermediate Similarity	NPC53520
0.7986	Intermediate Similarity	NPC306765
0.7986	Intermediate Similarity	NPC283088
0.7986	Intermediate Similarity	NPC249272
0.7986	Intermediate Similarity	NPC477596
0.7974	Intermediate Similarity	NPC124842
0.7973	Intermediate Similarity	NPC11314
0.7972	Intermediate Similarity	NPC327410
0.7972	Intermediate Similarity	NPC78307
0.7961	Intermediate Similarity	NPC142654
0.7959	Intermediate Similarity	NPC169452
0.7959	Intermediate Similarity	NPC181560
0.7958	Intermediate Similarity	NPC34070
0.7958	Intermediate Similarity	NPC469526
0.7958	Intermediate Similarity	NPC243305
0.7956	Intermediate Similarity	NPC139171
0.7956	Intermediate Similarity	NPC68167
0.7947	Intermediate Similarity	NPC476821
0.7945	Intermediate Similarity	NPC473622
0.7945	Intermediate Similarity	NPC141368
0.7943	Intermediate Similarity	NPC99731
0.7943	Intermediate Similarity	NPC146647

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 NPC23667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	927
0.2-0.3	1428
0.3-0.4	2786
0.4-0.5	2208
0.5-0.6	1061
0.6-0.7	376
0.7-0.8	33
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
0.8276	Intermediate Similarity	NPD8166	Discontinued
0.8028	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD2932	Approved
0.7868	Intermediate Similarity	NPD3019	Approved
0.7786	Intermediate Similarity	NPD1470	Approved
0.7697	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1201	Approved
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7574	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3300	Phase 2
0.7536	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3023	Approved
0.7429	Intermediate Similarity	NPD3026	Approved
0.741	Intermediate Similarity	NPD3024	Approved
0.741	Intermediate Similarity	NPD3025	Approved
0.7324	Intermediate Similarity	NPD9269	Phase 2
0.7324	Intermediate Similarity	NPD3972	Approved
0.7312	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD9494	Approved
0.729	Intermediate Similarity	NPD7390	Discontinued
0.7289	Intermediate Similarity	NPD7473	Discontinued
0.7285	Intermediate Similarity	NPD5408	Approved
0.7285	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD5405	Approved
0.7285	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6663	Approved
0.7205	Intermediate Similarity	NPD2801	Approved
0.7192	Intermediate Similarity	NPD5736	Approved
0.7179	Intermediate Similarity	NPD1511	Approved
0.717	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD1934	Approved
0.7133	Intermediate Similarity	NPD230	Phase 1
0.7124	Intermediate Similarity	NPD2344	Approved
0.7117	Intermediate Similarity	NPD3882	Suspended
0.7111	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6232	Discontinued
0.7105	Intermediate Similarity	NPD2799	Discontinued
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7089	Intermediate Similarity	NPD1512	Approved
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3226	Approved
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7055	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1164	Approved
0.705	Intermediate Similarity	NPD5951	Approved
0.7047	Intermediate Similarity	NPD3764	Approved
0.7042	Intermediate Similarity	NPD9268	Approved
0.7019	Intermediate Similarity	NPD7028	Phase 2
0.7014	Intermediate Similarity	NPD3092	Approved
0.7013	Intermediate Similarity	NPD2346	Discontinued
0.7013	Intermediate Similarity	NPD1471	Phase 3
0.7007	Intermediate Similarity	NPD2798	Approved
0.6994	Remote Similarity	NPD7819	Suspended
0.6987	Remote Similarity	NPD7003	Approved
0.6972	Remote Similarity	NPD3091	Approved
0.6971	Remote Similarity	NPD8434	Phase 2
0.6943	Remote Similarity	NPD6190	Approved
0.6943	Remote Similarity	NPD2309	Approved
0.6939	Remote Similarity	NPD3094	Phase 2
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1755	Approved
0.6914	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3020	Approved
0.6887	Remote Similarity	NPD8032	Phase 2
0.6883	Remote Similarity	NPD1510	Phase 2
0.6875	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4059	Approved
0.6875	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8150	Discontinued
0.6871	Remote Similarity	NPD1876	Approved
0.6863	Remote Similarity	NPD6651	Approved
0.6863	Remote Similarity	NPD1607	Approved
0.6849	Remote Similarity	NPD4878	Approved
0.6842	Remote Similarity	NPD1240	Approved
0.6842	Remote Similarity	NPD3818	Discontinued
0.6842	Remote Similarity	NPD3620	Phase 2
0.6842	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6099	Approved
0.6839	Remote Similarity	NPD6100	Approved
0.6835	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6166	Phase 2
0.6824	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2800	Approved
0.6813	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4380	Phase 2
0.6807	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5494	Approved
0.6783	Remote Similarity	NPD7610	Discontinued
0.6783	Remote Similarity	NPD5536	Phase 2
0.6779	Remote Similarity	NPD257	Approved
0.6779	Remote Similarity	NPD258	Approved
0.6772	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7075	Discontinued
0.6763	Remote Similarity	NPD7074	Phase 3
0.6763	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3095	Discontinued
0.6757	Remote Similarity	NPD1283	Approved
0.6752	Remote Similarity	NPD970	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3455	Phase 2
0.6747	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8127	Discontinued
0.6736	Remote Similarity	NPD9545	Approved
0.6718	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3268	Approved
0.6711	Remote Similarity	NPD2313	Discontinued
0.6708	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6599	Discontinued
0.6705	Remote Similarity	NPD7054	Approved
0.669	Remote Similarity	NPD1651	Approved
0.6688	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD1465	Phase 2
0.6687	Remote Similarity	NPD7236	Approved
0.6687	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5027	Approved
0.6686	Remote Similarity	NPD5029	Approved
0.6686	Remote Similarity	NPD5031	Approved
0.6686	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD7411	Suspended
0.6648	Remote Similarity	NPD4954	Approved
0.6648	Remote Similarity	NPD5034	Approved
0.6648	Remote Similarity	NPD5032	Approved
0.6648	Remote Similarity	NPD5026	Approved
0.6648	Remote Similarity	NPD5028	Approved
0.6648	Remote Similarity	NPD36	Approved
0.6648	Remote Similarity	NPD4955	Approved
0.6647	Remote Similarity	NPD5978	Approved
0.6647	Remote Similarity	NPD5977	Approved
0.6647	Remote Similarity	NPD3817	Phase 2
0.6646	Remote Similarity	NPD1549	Phase 2
0.6645	Remote Similarity	NPD7095	Approved
0.6645	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD826	Approved
0.6623	Remote Similarity	NPD825	Approved
0.6619	Remote Similarity	NPD74	Approved
0.6619	Remote Similarity	NPD9266	Approved
0.6618	Remote Similarity	NPD1929	Approved
0.6618	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1930	Approved
0.661	Remote Similarity	NPD5035	Approved
0.6609	Remote Similarity	NPD5844	Phase 1
0.6605	Remote Similarity	NPD2532	Approved
0.6605	Remote Similarity	NPD2533	Approved
0.6605	Remote Similarity	NPD2534	Approved
0.6597	Remote Similarity	NPD9493	Approved
0.6591	Remote Similarity	NPD2933	Approved
0.6591	Remote Similarity	NPD5030	Phase 2
0.6591	Remote Similarity	NPD7251	Discontinued
0.6591	Remote Similarity	NPD2934	Approved
0.6582	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7266	Discontinued
0.6582	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2629	Approved
0.6559	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1281	Approved
0.6554	Remote Similarity	NPD7808	Phase 3
0.655	Remote Similarity	NPD6959	Discontinued
0.6547	Remote Similarity	NPD9267	Approved
0.6547	Remote Similarity	NPD9264	Approved
0.6547	Remote Similarity	NPD9263	Approved
0.6538	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6797	Phase 2
0.6531	Remote Similarity	NPD1751	Approved
0.6529	Remote Similarity	NPD6234	Discontinued
0.6519	Remote Similarity	NPD2796	Approved
0.6519	Remote Similarity	NPD2066	Phase 3
0.6519	Remote Similarity	NPD6836	Approved
0.6517	Remote Similarity	NPD8312	Approved
0.6517	Remote Similarity	NPD8313	Approved
0.6514	Remote Similarity	NPD1221	Approved
0.6513	Remote Similarity	NPD9569	Approved
0.651	Remote Similarity	NPD1608	Approved
0.6509	Remote Similarity	NPD7768	Phase 2
0.6507	Remote Similarity	NPD7009	Phase 2
0.6503	Remote Similarity	NPD5283	Phase 1
0.65	Remote Similarity	NPD5037	Approved
0.65	Remote Similarity	NPD5038	Approved
0.6493	Remote Similarity	NPD3495	Discontinued
0.6493	Remote Similarity	NPD288	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