NPASS Compound

Structure

NPC237441 OpenBabel07101719142D 45 47 0 0 1 0 0 0 0 0999 V2000 1.6674 5.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8661 3.9832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0858 -1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2382 -3.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6102 -2.1639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8946 -0.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0464 2.6669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6076 4.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3583 -1.3370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3370 -1.3370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7348 3.1389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 3.5444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 -1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2832 3.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 -0.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 -0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7348 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3051 -1.0820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9649 -0.1642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 1.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1555 2.1602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9207 4.2365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2382 -2.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2700 -1.2462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3543 3.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4089 3.1056 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6953 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7348 1.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 1.6708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 -0.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4007 0.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7209 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 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 -5.5825 1.6708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 -1.2655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3118 1.3126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8668 -1.1902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 2.6495 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 26 2 0 0 0 0 8 26 1 0 0 0 0 9 37 1 0 0 0 0 10 37 1 0 0 0 0 11 45 1 0 0 0 0 12 14 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 15 17 2 0 0 0 0 15 27 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 20 27 2 0 0 0 0 20 31 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 22 38 1 0 0 0 0 26 28 1 0 0 0 0 27 33 1 0 0 0 0 28 14 1 1 0 0 0 29 16 1 6 0 0 0 29 37 1 0 0 0 0 30 31 2 0 0 0 0 30 40 1 0 0 0 0 31 45 1 0 0 0 0 32 33 1 0 0 0 0 32 34 2 0 0 0 0 32 35 1 0 0 0 0 33 41 2 0 0 0 0 34 38 1 0 0 0 0 34 42 1 0 0 0 0 35 39 1 0 0 0 0 35 43 2 0 0 0 0 36 38 1 0 0 0 0 36 39 1 0 0 0 0 36 44 2 0 0 0 0 37 39 1 0 0 0 0 38 21 1 6 0 0 0 39 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.38
Volume:	681.171
LogP:	8.809
LogD:	5.856
LogS:	-4.591
# Rotatable Bonds:	12
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	5.704
Fsp3:	0.538
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:	-4.928
MDCK Permeability:	1.349659578409046e-05
Pgp-inhibitor:	0.293
Pgp-substrate:	0.906
Human Intestinal Absorption (HIA):	0.085
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	96.10872650146484%
Volume Distribution (VD):	2.343
Pgp-substrate:	7.203346252441406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.798
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.835
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.486
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	14.264
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.772
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.85
Skin Sensitization:	0.039
Carcinogencity:	0.524
Eye Corrosion:	0.073
Eye Irritation:	0.151
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC237441

Natural Product ID:	NPC237441
*Common Name:**	IRGODUUTQDWGCW-OXWAJMPISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IRGODUUTQDWGCW-OXWAJMPISA-N
Standard InCHI:	InChI=1S/C39H52O6/c1-23(2)12-14-28(26(7)8)21-38-22-29(16-13-24(3)4)37(9,10)39(36(38)44,19-18-25(5)6)35(43)32(34(38)42)33(41)27-15-17-30(40)31(20-27)45-11/h12-13,15,17-18,20,28-29,40,42H,7,14,16,19,21-22H2,1-6,8-11H3/t28-,29+,38+,39-/m0/s1
SMILES:	CC(=CC[C@@H](C[C@@]12C[C@@H](CC=C(C)C)C(C)(C)[C@@](CC=C(C)C)(C(=O)C(=C1O)C(=O)c1ccc(c(c1)OC)O)C2=O)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505686
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:0001564] Bicyclic 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	1
Others	8

Activity Type	# Activity
Cell Line	4
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[533006]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[533006]
NPT2	Others	Unspecified		Activity	=	19.7	%	PMID[533006]
NPT2	Others	Unspecified		Activity	=	54.9	%	PMID[533006]
NPT2	Others	Unspecified		Activity	=	88.1	%	PMID[533006]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[533006]
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[533006]

☑ 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 NPC237441 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	396
0.1-0.2	1505
0.2-0.3	3166
0.3-0.4	7718
0.4-0.5	10554
0.5-0.6	4631
0.6-0.7	8260
0.7-0.8	6173
0.8-0.85	211
0.85-0.9	41
0.9-0.95	40
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC305710
0.9252	High Similarity	NPC46549
0.9252	High Similarity	NPC264229
0.9225	High Similarity	NPC42384
0.9225	High Similarity	NPC477849
0.9225	High Similarity	NPC157284
0.9225	High Similarity	NPC23667
0.9225	High Similarity	NPC473779
0.9225	High Similarity	NPC473479
0.9225	High Similarity	NPC289358
0.9225	High Similarity	NPC50615
0.9225	High Similarity	NPC165191
0.9225	High Similarity	NPC297797
0.9225	High Similarity	NPC46242
0.9225	High Similarity	NPC245760
0.9225	High Similarity	NPC114333
0.9225	High Similarity	NPC51531
0.9225	High Similarity	NPC5014
0.9225	High Similarity	NPC469857
0.9225	High Similarity	NPC28592
0.9225	High Similarity	NPC149773
0.9225	High Similarity	NPC91887
0.9161	High Similarity	NPC294330
0.9122	High Similarity	NPC132810
0.9116	High Similarity	NPC471970
0.911	High Similarity	NPC294679
0.911	High Similarity	NPC469375
0.911	High Similarity	NPC8493
0.911	High Similarity	NPC145301
0.911	High Similarity	NPC144247
0.9103	High Similarity	NPC471972
0.9103	High Similarity	NPC229218
0.9103	High Similarity	NPC141817
0.9103	High Similarity	NPC469855
0.9103	High Similarity	NPC176030
0.9103	High Similarity	NPC192597
0.9103	High Similarity	NPC30846
0.9103	High Similarity	NPC169214
0.9103	High Similarity	NPC471971
0.9097	High Similarity	NPC473527
0.9085	High Similarity	NPC7464
0.9054	High Similarity	NPC52692
0.8986	High Similarity	NPC273798
0.898	High Similarity	NPC469854
0.898	High Similarity	NPC469856
0.8912	High Similarity	NPC209085
0.8912	High Similarity	NPC224884
0.8851	High Similarity	NPC309169
0.8851	High Similarity	NPC196941
0.8828	High Similarity	NPC469681
0.8828	High Similarity	NPC471974
0.8828	High Similarity	NPC469680
0.8816	High Similarity	NPC144283
0.8792	High Similarity	NPC160777
0.8792	High Similarity	NPC73416
0.8784	High Similarity	NPC239608
0.8784	High Similarity	NPC46161
0.8776	High Similarity	NPC472410
0.8776	High Similarity	NPC84273
0.8741	High Similarity	NPC327410
0.8716	High Similarity	NPC11314
0.8693	High Similarity	NPC124842
0.8667	High Similarity	NPC225351
0.8636	High Similarity	NPC164912
0.863	High Similarity	NPC118366
0.8621	High Similarity	NPC88065
0.8621	High Similarity	NPC95485
0.8621	High Similarity	NPC89504
0.8592	High Similarity	NPC25736
0.859	High Similarity	NPC471968
0.8581	High Similarity	NPC82336
0.8581	High Similarity	NPC62051
0.8581	High Similarity	NPC78987
0.8571	High Similarity	NPC118427
0.8571	High Similarity	NPC478060
0.8571	High Similarity	NPC470377
0.8571	High Similarity	NPC473201
0.8571	High Similarity	NPC471975
0.8571	High Similarity	NPC470374
0.8571	High Similarity	NPC478059
0.8571	High Similarity	NPC302783
0.8544	High Similarity	NPC185617
0.8542	High Similarity	NPC50763
0.8533	High Similarity	NPC46880
0.8531	High Similarity	NPC66905
0.8506	High Similarity	NPC473579
0.8506	High Similarity	NPC475454
0.8506	High Similarity	NPC475311
0.8506	High Similarity	NPC473680
0.8506	High Similarity	NPC58310
0.8506	High Similarity	NPC295977
0.85	High Similarity	NPC100420
0.8497	Intermediate Similarity	NPC474903
0.8476	Intermediate Similarity	NPC471969
0.8471	Intermediate Similarity	NPC470762
0.8471	Intermediate Similarity	NPC474167
0.8462	Intermediate Similarity	NPC127172
0.8462	Intermediate Similarity	NPC304622
0.8452	Intermediate Similarity	NPC306011
0.8452	Intermediate Similarity	NPC472838
0.8451	Intermediate Similarity	NPC32163
0.8451	Intermediate Similarity	NPC16651
0.8431	Intermediate Similarity	NPC58373
0.8421	Intermediate Similarity	NPC258856
0.8414	Intermediate Similarity	NPC239302
0.8411	Intermediate Similarity	NPC50954
0.8408	Intermediate Similarity	NPC234485
0.8397	Intermediate Similarity	NPC312338
0.8397	Intermediate Similarity	NPC149889
0.8389	Intermediate Similarity	NPC474784
0.8389	Intermediate Similarity	NPC223336
0.8387	Intermediate Similarity	NPC472279
0.8387	Intermediate Similarity	NPC118033
0.8387	Intermediate Similarity	NPC48949
0.8367	Intermediate Similarity	NPC252343
0.8355	Intermediate Similarity	NPC91694
0.8355	Intermediate Similarity	NPC300603
0.8354	Intermediate Similarity	NPC472803
0.8354	Intermediate Similarity	NPC279605
0.8333	Intermediate Similarity	NPC28398
0.8333	Intermediate Similarity	NPC473773
0.8333	Intermediate Similarity	NPC75377
0.8333	Intermediate Similarity	NPC78505
0.8333	Intermediate Similarity	NPC475579
0.8323	Intermediate Similarity	NPC134293
0.8322	Intermediate Similarity	NPC276466
0.8322	Intermediate Similarity	NPC123722
0.8322	Intermediate Similarity	NPC151167
0.8322	Intermediate Similarity	NPC5018
0.8322	Intermediate Similarity	NPC123228
0.8312	Intermediate Similarity	NPC77598
0.8311	Intermediate Similarity	NPC324929
0.8302	Intermediate Similarity	NPC180011
0.8302	Intermediate Similarity	NPC161960
0.8302	Intermediate Similarity	NPC37543
0.8302	Intermediate Similarity	NPC178976
0.8302	Intermediate Similarity	NPC199463
0.8302	Intermediate Similarity	NPC187745
0.8302	Intermediate Similarity	NPC219867
0.8302	Intermediate Similarity	NPC304008
0.8301	Intermediate Similarity	NPC75295
0.8291	Intermediate Similarity	NPC38898
0.8291	Intermediate Similarity	NPC472048
0.8289	Intermediate Similarity	NPC469615
0.8288	Intermediate Similarity	NPC153453
0.8282	Intermediate Similarity	NPC200726
0.8282	Intermediate Similarity	NPC263212
0.828	Intermediate Similarity	NPC474993
0.8276	Intermediate Similarity	NPC172673
0.8269	Intermediate Similarity	NPC475718
0.8261	Intermediate Similarity	NPC472906
0.8258	Intermediate Similarity	NPC55327
0.8255	Intermediate Similarity	NPC471152
0.8252	Intermediate Similarity	NPC127937
0.8252	Intermediate Similarity	NPC84076
0.8252	Intermediate Similarity	NPC179777
0.8252	Intermediate Similarity	NPC303680
0.8252	Intermediate Similarity	NPC92207
0.8252	Intermediate Similarity	NPC90128
0.825	Intermediate Similarity	NPC235448
0.8247	Intermediate Similarity	NPC39361
0.8239	Intermediate Similarity	NPC77807
0.8239	Intermediate Similarity	NPC312404
0.8239	Intermediate Similarity	NPC273686
0.8239	Intermediate Similarity	NPC5379
0.8239	Intermediate Similarity	NPC14561
0.8239	Intermediate Similarity	NPC115853
0.8239	Intermediate Similarity	NPC213401
0.8235	Intermediate Similarity	NPC207732
0.8235	Intermediate Similarity	NPC469683
0.8235	Intermediate Similarity	NPC142165
0.8232	Intermediate Similarity	NPC177362
0.8231	Intermediate Similarity	NPC474715
0.8231	Intermediate Similarity	NPC138472
0.8231	Intermediate Similarity	NPC4170
0.8228	Intermediate Similarity	NPC25127
0.8228	Intermediate Similarity	NPC477047
0.8228	Intermediate Similarity	NPC477048
0.8224	Intermediate Similarity	NPC137920
0.8224	Intermediate Similarity	NPC125134
0.8224	Intermediate Similarity	NPC86455
0.8221	Intermediate Similarity	NPC26386
0.8217	Intermediate Similarity	NPC256406
0.8212	Intermediate Similarity	NPC470035
0.821	Intermediate Similarity	NPC149389
0.8205	Intermediate Similarity	NPC69430
0.8205	Intermediate Similarity	NPC264550
0.8205	Intermediate Similarity	NPC264289
0.8205	Intermediate Similarity	NPC139293
0.8205	Intermediate Similarity	NPC195763
0.8205	Intermediate Similarity	NPC142876
0.8205	Intermediate Similarity	NPC200060
0.8205	Intermediate Similarity	NPC261322
0.8205	Intermediate Similarity	NPC40290
0.8205	Intermediate Similarity	NPC333691
0.8205	Intermediate Similarity	NPC37220
0.82	Intermediate Similarity	NPC132723
0.82	Intermediate Similarity	NPC325625
0.82	Intermediate Similarity	NPC76032
0.8194	Intermediate Similarity	NPC470757

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 NPC237441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	930
0.2-0.3	1512
0.3-0.4	2586
0.4-0.5	2135
0.5-0.6	1049
0.6-0.7	486
0.7-0.8	100
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
0.8158	Intermediate Similarity	NPD8166	Discontinued
0.8069	Intermediate Similarity	NPD9494	Approved
0.8042	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.7888	Intermediate Similarity	NPD2801	Approved
0.7847	Intermediate Similarity	NPD3972	Approved
0.7826	Intermediate Similarity	NPD1934	Approved
0.7791	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.775	Intermediate Similarity	NPD7458	Discontinued
0.7714	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7028	Phase 2
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7566	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3620	Phase 2
0.7552	Intermediate Similarity	NPD5536	Phase 2
0.7548	Intermediate Similarity	NPD2935	Discontinued
0.7547	Intermediate Similarity	NPD1511	Approved
0.7543	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7471	Intermediate Similarity	NPD6166	Phase 2
0.7471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7003	Approved
0.7455	Intermediate Similarity	NPD7819	Suspended
0.7453	Intermediate Similarity	NPD1512	Approved
0.7451	Intermediate Similarity	NPD943	Approved
0.744	Intermediate Similarity	NPD5494	Approved
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2798	Approved
0.7399	Intermediate Similarity	NPD7074	Phase 3
0.7397	Intermediate Similarity	NPD2932	Approved
0.7396	Intermediate Similarity	NPD8127	Discontinued
0.7389	Intermediate Similarity	NPD2346	Discontinued
0.7389	Intermediate Similarity	NPD1471	Phase 3
0.7383	Intermediate Similarity	NPD1876	Approved
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.7372	Intermediate Similarity	NPD1510	Phase 2
0.7365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4110	Phase 3
0.7355	Intermediate Similarity	NPD1607	Approved
0.7355	Intermediate Similarity	NPD6651	Approved
0.7346	Intermediate Similarity	NPD6273	Approved
0.7341	Intermediate Similarity	NPD7054	Approved
0.7338	Intermediate Similarity	NPD1240	Approved
0.7333	Intermediate Similarity	NPD6873	Phase 2
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.7314	Intermediate Similarity	NPD7685	Pre-registration
0.7312	Intermediate Similarity	NPD2309	Approved
0.7305	Intermediate Similarity	NPD3817	Phase 2
0.7305	Intermediate Similarity	NPD5978	Approved
0.7305	Intermediate Similarity	NPD5977	Approved
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7472	Approved
0.729	Intermediate Similarity	NPD447	Suspended
0.7284	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3019	Approved
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD8032	Phase 2
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD1283	Approved
0.7254	Intermediate Similarity	NPD228	Approved
0.7246	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1465	Phase 2
0.7241	Intermediate Similarity	NPD5844	Phase 1
0.7233	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1470	Approved
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD6100	Approved
0.7211	Intermediate Similarity	NPD1651	Approved
0.7188	Intermediate Similarity	NPD2800	Approved
0.7179	Intermediate Similarity	NPD230	Phase 1
0.7176	Intermediate Similarity	NPD6234	Discontinued
0.7175	Intermediate Similarity	NPD7808	Phase 3
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7411	Suspended
0.7125	Intermediate Similarity	NPD1549	Phase 2
0.7119	Intermediate Similarity	NPD7251	Discontinued
0.711	Intermediate Similarity	NPD3926	Phase 2
0.7108	Intermediate Similarity	NPD824	Approved
0.7097	Intermediate Similarity	NPD3268	Approved
0.7097	Intermediate Similarity	NPD2313	Discontinued
0.7083	Intermediate Similarity	NPD37	Approved
0.7079	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2534	Approved
0.7073	Intermediate Similarity	NPD2533	Approved
0.7073	Intermediate Similarity	NPD2532	Approved
0.7073	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1201	Approved
0.7067	Intermediate Similarity	NPD1281	Approved
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6797	Phase 2
0.7062	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3300	Phase 2
0.7049	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD3750	Approved
0.7032	Intermediate Similarity	NPD3027	Phase 3
0.7024	Intermediate Similarity	NPD6386	Approved
0.7024	Intermediate Similarity	NPD6385	Approved
0.7018	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8150	Discontinued
0.7012	Intermediate Similarity	NPD6799	Approved
0.7007	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD2796	Approved
0.6994	Remote Similarity	NPD6959	Discontinued
0.6994	Remote Similarity	NPD1247	Approved
0.6994	Remote Similarity	NPD6190	Approved
0.6993	Remote Similarity	NPD3021	Approved
0.6993	Remote Similarity	NPD3022	Approved
0.6989	Remote Similarity	NPD7228	Approved
0.6987	Remote Similarity	NPD3764	Approved
0.6982	Remote Similarity	NPD6801	Discontinued
0.698	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6355	Discontinued
0.6962	Remote Similarity	NPD1933	Approved
0.6959	Remote Similarity	NPD4966	Approved
0.6959	Remote Similarity	NPD4965	Approved
0.6959	Remote Similarity	NPD7768	Phase 2
0.6959	Remote Similarity	NPD4967	Phase 2
0.6949	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6663	Approved
0.6941	Remote Similarity	NPD5761	Phase 2
0.6941	Remote Similarity	NPD5760	Phase 2
0.6937	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4626	Approved
0.6918	Remote Similarity	NPD1241	Discontinued
0.6908	Remote Similarity	NPD1608	Approved
0.6905	Remote Similarity	NPD3455	Phase 2
0.6905	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5736	Approved
0.6899	Remote Similarity	NPD2979	Phase 3
0.6894	Remote Similarity	NPD2438	Suspended
0.689	Remote Similarity	NPD2354	Approved
0.6887	Remote Similarity	NPD3023	Approved
0.6887	Remote Similarity	NPD3026	Approved
0.6867	Remote Similarity	NPD3024	Approved
0.6867	Remote Similarity	NPD3025	Approved
0.6863	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3657	Discovery
0.6855	Remote Similarity	NPD5735	Approved
0.6842	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4624	Approved
0.6833	Remote Similarity	NPD6559	Discontinued
0.6824	Remote Similarity	NPD7157	Approved
0.6824	Remote Similarity	NPD7110	Phase 1
0.6824	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3749	Approved
0.6815	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD2488	Approved
0.6811	Remote Similarity	NPD2490	Approved
0.6807	Remote Similarity	NPD7390	Discontinued
0.6806	Remote Similarity	NPD2491	Approved
0.6802	Remote Similarity	NPD2296	Approved
0.68	Remote Similarity	NPD9545	Approved
0.68	Remote Similarity	NPD7199	Phase 2
0.6798	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9269	Phase 2
0.6792	Remote Similarity	NPD4140	Approved
0.679	Remote Similarity	NPD5406	Approved
0.679	Remote Similarity	NPD5405	Approved
0.679	Remote Similarity	NPD5408	Approved
0.679	Remote Similarity	NPD5404	Approved
0.6786	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7577	Discontinued
0.6782	Remote Similarity	NPD919	Approved
0.6782	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2898	Approved
0.6774	Remote Similarity	NPD2797	Approved
0.6774	Remote Similarity	NPD3266	Approved
0.6774	Remote Similarity	NPD1203	Approved
0.6774	Remote Similarity	NPD3267	Approved
0.6772	Remote Similarity	NPD6798	Discontinued
0.6766	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6875	Approved
0.6765	Remote Similarity	NPD6876	Approved
0.6753	Remote Similarity	NPD5327	Phase 3
0.6752	Remote Similarity	NPD6832	Phase 2
0.6748	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7236	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