NPASS Compound

Structure

NPC305710 OpenBabel07101719152D 45 48 0 0 1 0 0 0 0 0999 V2000 -5.6318 1.7971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7658 3.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9627 3.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2740 4.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2375 -3.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9838 -4.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5337 -1.5689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0337 -0.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8517 1.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1465 0.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6699 2.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8997 1.7971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7846 2.5455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8039 -1.4959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8997 0.7971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1710 2.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6699 -0.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5757 -2.8862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8576 -1.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9379 0.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1677 0.7971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1301 1.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7658 2.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0071 3.5204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2657 -3.6101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9379 -0.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0337 0.2971 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3935 1.2758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6699 0.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8039 0.5041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7942 -0.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0718 -1.4959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -1.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 -0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3017 -0.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0337 -0.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3017 0.2971 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1677 -1.2029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5359 0.5041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0718 -2.4959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2820 -2.4189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4356 -1.2029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8039 1.5041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 36 1 0 0 0 0 8 36 1 0 0 0 0 9 37 1 0 0 0 0 10 37 1 0 0 0 0 11 44 1 0 0 0 0 12 15 1 0 0 0 0 12 23 2 0 0 0 0 13 16 1 0 0 0 0 13 24 2 0 0 0 0 14 17 2 0 0 0 0 14 26 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 22 38 1 0 0 0 0 26 32 1 0 0 0 0 27 15 1 6 0 0 0 27 36 1 0 0 0 0 28 16 1 6 0 0 0 28 37 1 0 0 0 0 29 30 2 0 0 0 0 29 40 1 0 0 0 0 30 44 1 0 0 0 0 31 32 1 0 0 0 0 31 33 1 0 0 0 0 31 34 2 0 0 0 0 32 41 2 0 0 0 0 33 39 1 0 0 0 0 33 42 2 0 0 0 0 34 38 1 0 0 0 0 34 45 1 0 0 0 0 35 38 1 0 0 0 0 35 39 1 0 0 0 0 35 43 2 0 0 0 0 36 39 1 0 0 0 0 37 45 1 0 0 0 0 38 21 1 6 0 0 0 39 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.38
Volume:	675.251
LogP:	9.057
LogD:	5.934
LogS:	-4.747
# Rotatable Bonds:	9
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	6.069
Fsp3:	0.564
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.946
MDCK Permeability:	1.3410537576419301e-05
Pgp-inhibitor:	0.365
Pgp-substrate:	0.397
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	92.96231079101562%
Volume Distribution (VD):	1.673
Pgp-substrate:	8.778573989868164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.328
CYP2C19-inhibitor:	0.818
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.807
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.802

ADMET: Excretion

Clearance (CL):	11.201
Half-life (T1/2):	0.024

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.63
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.031
Carcinogencity:	0.344
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC305710

Natural Product ID:	NPC305710
*Common Name:**	KMXJENAJTXOUOJ-OAKZDBKWSA-N
IUPAC Name:	n.a.
Synonyms:	Isogarcinol 13-O-Methyl Ether
Standard InCHIKey:	KMXJENAJTXOUOJ-OAKZDBKWSA-N
Standard InCHI:	InChI=1S/C39H52O6/c1-23(2)12-15-27-21-38-22-28(16-13-24(3)4)37(9,10)45-34(38)31(32(41)26-14-17-29(40)30(20-26)44-11)33(42)39(35(38)43,36(27,7)8)19-18-25(5)6/h12-14,17-18,20,27-28,40H,15-16,19,21-22H2,1-11H3/t27-,28+,38+,39+/m1/s1
SMILES:	CC(=CC[C@@H]1C[C@]23C[C@H](CC=C(C)C)C(C)(C)OC2=C(C(=O)c2ccc(c(c2)OC)O)C(=O)[C@@](CC=C(C)C)(C3=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502089
PubChem CID:	11114773
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
NPO33514	garcinia assigu	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608850]

☑ 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	8

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[448540]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[448540]
NPT1079	Individual Protein	Histone acetyltransferase p300	Homo sapiens	IC50	=	5000.0	nM	PMID[448541]
NPT2	Others	Unspecified		Activity	=	18.5	%	PMID[448540]
NPT2	Others	Unspecified		Activity	=	60.1	%	PMID[448540]
NPT2	Others	Unspecified		Activity	=	89.0	%	PMID[448540]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[448540]
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[448540]

☑ 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 NPC305710 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	412
0.1-0.2	1532
0.2-0.3	3067
0.3-0.4	7418
0.4-0.5	10579
0.5-0.6	5331
0.6-0.7	8306
0.7-0.8	5868
0.8-0.85	120
0.85-0.9	52
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC237441
0.9392	High Similarity	NPC46549
0.9392	High Similarity	NPC264229
0.9384	High Similarity	NPC8493
0.9384	High Similarity	NPC144247
0.9384	High Similarity	NPC145301
0.9384	High Similarity	NPC294679
0.9384	High Similarity	NPC469375
0.9133	High Similarity	NPC132810
0.9041	High Similarity	NPC294330
0.9	High Similarity	NPC471970
0.9	High Similarity	NPC273798
0.8973	High Similarity	NPC473479
0.8973	High Similarity	NPC114333
0.8973	High Similarity	NPC245760
0.8973	High Similarity	NPC289358
0.8973	High Similarity	NPC28592
0.8973	High Similarity	NPC149773
0.8973	High Similarity	NPC469857
0.8973	High Similarity	NPC23667
0.8973	High Similarity	NPC51531
0.8973	High Similarity	NPC50615
0.8973	High Similarity	NPC473779
0.8973	High Similarity	NPC477849
0.8973	High Similarity	NPC5014
0.8973	High Similarity	NPC165191
0.8973	High Similarity	NPC46242
0.8973	High Similarity	NPC91887
0.8973	High Similarity	NPC157284
0.8973	High Similarity	NPC42384
0.8973	High Similarity	NPC297797
0.8867	High Similarity	NPC469854
0.8867	High Similarity	NPC469856
0.8859	High Similarity	NPC229218
0.8859	High Similarity	NPC141817
0.8859	High Similarity	NPC469855
0.8859	High Similarity	NPC192597
0.8859	High Similarity	NPC471972
0.8859	High Similarity	NPC30846
0.8859	High Similarity	NPC169214
0.8859	High Similarity	NPC471971
0.8859	High Similarity	NPC176030
0.8851	High Similarity	NPC473527
0.8846	High Similarity	NPC471968
0.8836	High Similarity	NPC7464
0.8816	High Similarity	NPC52692
0.88	High Similarity	NPC209085
0.88	High Similarity	NPC224884
0.8776	High Similarity	NPC118366
0.8716	High Similarity	NPC471974
0.8716	High Similarity	NPC469681
0.8716	High Similarity	NPC469680
0.871	High Similarity	NPC144283
0.8667	High Similarity	NPC472410
0.863	High Similarity	NPC327410
0.8618	High Similarity	NPC309169
0.8618	High Similarity	NPC196941
0.8589	High Similarity	NPC470374
0.8589	High Similarity	NPC478059
0.8589	High Similarity	NPC478060
0.8589	High Similarity	NPC470377
0.8589	High Similarity	NPC471975
0.8562	High Similarity	NPC73416
0.8562	High Similarity	NPC160777
0.8553	High Similarity	NPC239608
0.8553	High Similarity	NPC46161
0.8543	High Similarity	NPC84273
0.8509	High Similarity	NPC472906
0.8494	Intermediate Similarity	NPC471969
0.8487	Intermediate Similarity	NPC11314
0.8485	Intermediate Similarity	NPC472803
0.8471	Intermediate Similarity	NPC124842
0.8447	Intermediate Similarity	NPC185617
0.8442	Intermediate Similarity	NPC225351
0.8418	Intermediate Similarity	NPC164912
0.8415	Intermediate Similarity	NPC263212
0.8408	Intermediate Similarity	NPC475454
0.8408	Intermediate Similarity	NPC475311
0.8408	Intermediate Similarity	NPC58310
0.8408	Intermediate Similarity	NPC295977
0.8408	Intermediate Similarity	NPC473680
0.8408	Intermediate Similarity	NPC118033
0.8408	Intermediate Similarity	NPC473579
0.8405	Intermediate Similarity	NPC100420
0.8395	Intermediate Similarity	NPC234644
0.8395	Intermediate Similarity	NPC57715
0.8389	Intermediate Similarity	NPC88065
0.8389	Intermediate Similarity	NPC95485
0.8389	Intermediate Similarity	NPC89504
0.8365	Intermediate Similarity	NPC62051
0.8356	Intermediate Similarity	NPC25736
0.8355	Intermediate Similarity	NPC82336
0.8355	Intermediate Similarity	NPC78987
0.8354	Intermediate Similarity	NPC472838
0.8354	Intermediate Similarity	NPC473773
0.8354	Intermediate Similarity	NPC302783
0.8354	Intermediate Similarity	NPC306011
0.8354	Intermediate Similarity	NPC475579
0.8354	Intermediate Similarity	NPC473201
0.8354	Intermediate Similarity	NPC118427
0.8333	Intermediate Similarity	NPC188433
0.8323	Intermediate Similarity	NPC180011
0.8323	Intermediate Similarity	NPC161960
0.8323	Intermediate Similarity	NPC187745
0.8323	Intermediate Similarity	NPC268602
0.8323	Intermediate Similarity	NPC219867
0.8323	Intermediate Similarity	NPC472963
0.8323	Intermediate Similarity	NPC304008
0.8312	Intermediate Similarity	NPC46880
0.8311	Intermediate Similarity	NPC50763
0.8303	Intermediate Similarity	NPC200726
0.8299	Intermediate Similarity	NPC66905
0.8291	Intermediate Similarity	NPC475718
0.828	Intermediate Similarity	NPC474903
0.8278	Intermediate Similarity	NPC471152
0.8272	Intermediate Similarity	NPC235448
0.8272	Intermediate Similarity	NPC204879
0.8261	Intermediate Similarity	NPC288353
0.8261	Intermediate Similarity	NPC279605
0.8261	Intermediate Similarity	NPC472907
0.8261	Intermediate Similarity	NPC470762
0.8261	Intermediate Similarity	NPC474167
0.8261	Intermediate Similarity	NPC115853
0.8253	Intermediate Similarity	NPC193222
0.8253	Intermediate Similarity	NPC177362
0.825	Intermediate Similarity	NPC472905
0.825	Intermediate Similarity	NPC127172
0.825	Intermediate Similarity	NPC475770
0.8232	Intermediate Similarity	NPC474150
0.8232	Intermediate Similarity	NPC474162
0.8231	Intermediate Similarity	NPC304622
0.8228	Intermediate Similarity	NPC472837
0.8224	Intermediate Similarity	NPC132723
0.8224	Intermediate Similarity	NPC76032
0.8221	Intermediate Similarity	NPC474960
0.8221	Intermediate Similarity	NPC471973
0.8219	Intermediate Similarity	NPC32163
0.8219	Intermediate Similarity	NPC16651
0.8217	Intermediate Similarity	NPC58373
0.821	Intermediate Similarity	NPC296044
0.821	Intermediate Similarity	NPC299520
0.821	Intermediate Similarity	NPC218313
0.821	Intermediate Similarity	NPC129684
0.821	Intermediate Similarity	NPC474681
0.821	Intermediate Similarity	NPC136674
0.821	Intermediate Similarity	NPC167098
0.8205	Intermediate Similarity	NPC258856
0.8204	Intermediate Similarity	NPC288813
0.8204	Intermediate Similarity	NPC266545
0.8204	Intermediate Similarity	NPC202428
0.8199	Intermediate Similarity	NPC230149
0.8199	Intermediate Similarity	NPC152951
0.8199	Intermediate Similarity	NPC117992
0.8199	Intermediate Similarity	NPC168247
0.8199	Intermediate Similarity	NPC256925
0.8199	Intermediate Similarity	NPC57674
0.8199	Intermediate Similarity	NPC234485
0.8194	Intermediate Similarity	NPC50954
0.8194	Intermediate Similarity	NPC469615
0.8193	Intermediate Similarity	NPC476056
0.8193	Intermediate Similarity	NPC39091
0.8188	Intermediate Similarity	NPC239302
0.8187	Intermediate Similarity	NPC205392
0.8187	Intermediate Similarity	NPC105942
0.8187	Intermediate Similarity	NPC149889
0.8187	Intermediate Similarity	NPC312338
0.8182	Intermediate Similarity	NPC220313
0.8182	Intermediate Similarity	NPC12461
0.8182	Intermediate Similarity	NPC303460
0.8182	Intermediate Similarity	NPC187491
0.8182	Intermediate Similarity	NPC319200
0.8182	Intermediate Similarity	NPC306321
0.8176	Intermediate Similarity	NPC48949
0.8176	Intermediate Similarity	NPC475054
0.8176	Intermediate Similarity	NPC472279
0.8171	Intermediate Similarity	NPC472275
0.817	Intermediate Similarity	NPC474784
0.817	Intermediate Similarity	NPC223336
0.8165	Intermediate Similarity	NPC474556
0.816	Intermediate Similarity	NPC197856
0.8148	Intermediate Similarity	NPC472455
0.8148	Intermediate Similarity	NPC478223
0.8148	Intermediate Similarity	NPC470600
0.8148	Intermediate Similarity	NPC5322
0.8148	Intermediate Similarity	NPC133970
0.8148	Intermediate Similarity	NPC6633
0.8146	Intermediate Similarity	NPC252343
0.8144	Intermediate Similarity	NPC476306
0.8144	Intermediate Similarity	NPC218226
0.8141	Intermediate Similarity	NPC280717
0.8141	Intermediate Similarity	NPC271607
0.8141	Intermediate Similarity	NPC91694
0.8141	Intermediate Similarity	NPC469683
0.8141	Intermediate Similarity	NPC307205
0.8141	Intermediate Similarity	NPC300603
0.8137	Intermediate Similarity	NPC49402
0.8137	Intermediate Similarity	NPC474000
0.8137	Intermediate Similarity	NPC70433
0.8137	Intermediate Similarity	NPC273462
0.8137	Intermediate Similarity	NPC227337

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 NPC305710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	935
0.2-0.3	1514
0.3-0.4	2636
0.4-0.5	2149
0.5-0.6	1002
0.6-0.7	471
0.7-0.8	79
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD8166	Discontinued
0.7853	Intermediate Similarity	NPD1934	Approved
0.7852	Intermediate Similarity	NPD9494	Approved
0.7823	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD2801	Approved
0.7771	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7473	Discontinued
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7028	Phase 2
0.7711	Intermediate Similarity	NPD3882	Suspended
0.7669	Intermediate Similarity	NPD7458	Discontinued
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3972	Approved
0.761	Intermediate Similarity	NPD4628	Phase 3
0.7602	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6166	Phase 2
0.7588	Intermediate Similarity	NPD6232	Discontinued
0.7574	Intermediate Similarity	NPD5494	Approved
0.7557	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7685	Pre-registration
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7528	Intermediate Similarity	NPD8434	Phase 2
0.7515	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7471	Intermediate Similarity	NPD7054	Approved
0.7469	Intermediate Similarity	NPD1511	Approved
0.7429	Intermediate Similarity	NPD7472	Approved
0.7427	Intermediate Similarity	NPD8127	Discontinued
0.7421	Intermediate Similarity	NPD2344	Approved
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7414	Intermediate Similarity	NPD3818	Discontinued
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD7003	Approved
0.7381	Intermediate Similarity	NPD1465	Phase 2
0.7378	Intermediate Similarity	NPD6273	Approved
0.7378	Intermediate Similarity	NPD1512	Approved
0.7372	Intermediate Similarity	NPD3620	Phase 2
0.7372	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5844	Phase 1
0.7362	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2935	Discontinued
0.7358	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD6099	Approved
0.7353	Intermediate Similarity	NPD7075	Discontinued
0.7349	Intermediate Similarity	NPD3226	Approved
0.7347	Intermediate Similarity	NPD5536	Phase 2
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1471	Phase 3
0.7303	Intermediate Similarity	NPD7808	Phase 3
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4110	Phase 3
0.7284	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7411	Suspended
0.7261	Intermediate Similarity	NPD943	Approved
0.7247	Intermediate Similarity	NPD7251	Discontinued
0.7239	Intermediate Similarity	NPD2309	Approved
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7235	Intermediate Similarity	NPD3817	Phase 2
0.7235	Intermediate Similarity	NPD5978	Approved
0.7235	Intermediate Similarity	NPD5977	Approved
0.7215	Intermediate Similarity	NPD447	Suspended
0.7212	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2798	Approved
0.7207	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6599	Discontinued
0.72	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2932	Approved
0.7197	Intermediate Similarity	NPD8032	Phase 2
0.7191	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6797	Phase 2
0.719	Intermediate Similarity	NPD1876	Approved
0.7188	Intermediate Similarity	NPD1510	Phase 2
0.7181	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7095	Approved
0.717	Intermediate Similarity	NPD1607	Approved
0.717	Intermediate Similarity	NPD6651	Approved
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.716	Intermediate Similarity	NPD6873	Phase 2
0.716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1240	Approved
0.7151	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6959	Discontinued
0.7126	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7228	Approved
0.7117	Intermediate Similarity	NPD2800	Approved
0.711	Intermediate Similarity	NPD6234	Discontinued
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7099	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3300	Phase 2
0.7086	Intermediate Similarity	NPD3019	Approved
0.7079	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1283	Approved
0.7075	Intermediate Similarity	NPD5283	Phase 1
0.7073	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD228	Approved
0.7052	Intermediate Similarity	NPD3749	Approved
0.7045	Intermediate Similarity	NPD3926	Phase 2
0.7041	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1470	Approved
0.703	Intermediate Similarity	NPD6190	Approved
0.7025	Intermediate Similarity	NPD2313	Discontinued
0.7025	Intermediate Similarity	NPD3268	Approved
0.7025	Intermediate Similarity	NPD3764	Approved
0.702	Intermediate Similarity	NPD1651	Approved
0.7018	Intermediate Similarity	NPD7577	Discontinued
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD1933	Approved
0.6994	Remote Similarity	NPD7768	Phase 2
0.6977	Remote Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD5761	Phase 2
0.6975	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6386	Approved
0.6959	Remote Similarity	NPD6385	Approved
0.6946	Remote Similarity	NPD6799	Approved
0.6941	Remote Similarity	NPD824	Approved
0.6937	Remote Similarity	NPD4060	Phase 1
0.6935	Remote Similarity	NPD2490	Approved
0.6935	Remote Similarity	NPD2488	Approved
0.6933	Remote Similarity	NPD2796	Approved
0.6932	Remote Similarity	NPD1247	Approved
0.6931	Remote Similarity	NPD7907	Approved
0.6928	Remote Similarity	NPD2354	Approved
0.6927	Remote Similarity	NPD2491	Approved
0.6927	Remote Similarity	NPD3751	Discontinued
0.6919	Remote Similarity	NPD37	Approved
0.6919	Remote Similarity	NPD6801	Discontinued
0.6905	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4967	Phase 2
0.6897	Remote Similarity	NPD4965	Approved
0.6897	Remote Similarity	NPD4966	Approved
0.6894	Remote Similarity	NPD6355	Discontinued
0.6886	Remote Similarity	NPD7236	Approved
0.6883	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1201	Approved
0.6883	Remote Similarity	NPD1281	Approved
0.6875	Remote Similarity	NPD6663	Approved
0.6868	Remote Similarity	NPD6559	Discontinued
0.6855	Remote Similarity	NPD3027	Phase 3
0.6846	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD3455	Phase 2
0.6839	Remote Similarity	NPD3448	Approved
0.6839	Remote Similarity	NPD1608	Approved
0.6839	Remote Similarity	NPD3057	Approved
0.6835	Remote Similarity	NPD5736	Approved
0.6832	Remote Similarity	NPD4665	Approved
0.6832	Remote Similarity	NPD4111	Phase 1
0.6832	Remote Similarity	NPD2979	Phase 3
0.6829	Remote Similarity	NPD2438	Suspended
0.6824	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6782	Approved
0.6823	Remote Similarity	NPD6781	Approved
0.6823	Remote Similarity	NPD6777	Approved
0.6823	Remote Similarity	NPD6779	Approved
0.6823	Remote Similarity	NPD6780	Approved
0.6823	Remote Similarity	NPD6778	Approved
0.6823	Remote Similarity	NPD6776	Approved
0.6821	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6844	Discontinued
0.6818	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7097	Phase 1
0.6804	Remote Similarity	NPD7435	Discontinued
0.6804	Remote Similarity	NPD7697	Approved
0.6804	Remote Similarity	NPD7696	Phase 3
0.6804	Remote Similarity	NPD7698	Approved
0.6803	Remote Similarity	NPD3021	Approved
0.6803	Remote Similarity	NPD3022	Approved
0.6797	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5735	Approved
0.6788	Remote Similarity	NPD2494	Approved
0.6788	Remote Similarity	NPD7266	Discontinued
0.6788	Remote Similarity	NPD2493	Approved
0.6776	Remote Similarity	NPD6765	Approved
0.6776	Remote Similarity	NPD6764	Approved
0.6772	Remote Similarity	NPD4624	Approved
0.6769	Remote Similarity	NPD4583	Approved
0.6769	Remote Similarity	NPD7870	Phase 2
0.6769	Remote Similarity	NPD7871	Phase 2
0.6769	Remote Similarity	NPD4582	Approved
0.6768	Remote Similarity	NPD4308	Phase 3
0.6768	Remote Similarity	NPD3748	Approved
0.6763	Remote Similarity	NPD7110	Phase 1
0.6763	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7157	Approved
0.6753	Remote Similarity	NPD4626	Approved
0.6753	Remote Similarity	NPD3533	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