NPASS Compound

Structure

CID5046 OpenBabel06191715322D 31 35 0 0 1 0 0 0 0 0999 V2000 -6.3552 3.2493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0991 2.1190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0500 4.6996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8854 3.1642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -2.9614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6921 1.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6912 -1.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7940 3.5694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4923 2.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8453 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3821 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3818 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6909 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8462 1.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4009 3.0467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7483 3.7719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5380 2.4391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6915 -1.9526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5377 1.4635 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8462 -1.4646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5365 -1.4641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8456 -0.4885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 0.9755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6915 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4027 -1.9637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 1 0 0 0 21 23 1 0 0 0 0 22 5 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 27 1 6 0 0 0 24 29 1 6 0 0 0 25 31 1 1 0 0 0 26 28 1 1 0 0 0 26 30 1 0 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	490.807
LogP:	7.52
LogD:	5.811
LogS:	-6.857
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	5.579
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.878
MDCK Permeability:	1.1689648999890778e-05
Pgp-inhibitor:	0.136
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	94.72298431396484%
Volume Distribution (VD):	1.378
Pgp-substrate:	1.8120537996292114%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.45
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.192
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.202
CYP2D6-substrate:	0.62
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.856

ADMET: Excretion

Clearance (CL):	7.037
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.933
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.809
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.933
Carcinogencity:	0.266
Eye Corrosion:	0.256
Eye Irritation:	0.084
Respiratory Toxicity:	0.632

Download Data

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

Natural Product: NPC5046

Natural Product ID:	NPC5046
*Common Name:**	HUNLTIZKNQDZEI-JXXYSSPJSA-N
IUPAC Name:	n.a.
Synonyms:	3-Epicycloeucalenol
Standard InCHIKey:	HUNLTIZKNQDZEI-JXXYSSPJSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-19(2)20(3)8-9-21(4)23-12-14-28(7)26-11-10-24-22(5)25(31)13-15-29(24)18-30(26,29)17-16-27(23,28)6/h19,21-26,31H,3,8-18H2,1-2,4-7H3/t21-,22+,23-,24+,25-,26+,27-,28+,29-,30+/m1/s1
SMILES:	C=C(C(C)C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@H]([C@H]2C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390109
PubChem CID:	44423591
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[136119]
NPO16746	Lendenfeldia frondosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402955]
NPO33305	musa sapientum	Species	Musaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24680612]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19073	Uncaria lancifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16040	Pristimera indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO3022	Toxicopueraria peduncularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19073	Uncaria lancifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16040	Pristimera indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11777	Pluchea sericea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17440	Thryptomene kochii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18830	Valeriana cardamines	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19753	Liabum bourgeaui	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14711.1	Arabidopsis lyrata subsp. lyrata	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16040	Pristimera indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19073	Uncaria lancifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23370	Sticta mougeotiana	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29099	Sinocrassula indica	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19692	Quercus variabilis	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11042	Lecanora sordida	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11777	Pluchea sericea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28174	Poterium sanguisorba	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16746	Lendenfeldia frondosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18008	Viburnum rhytidophyllum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13673	Ipomoea muelleri	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18497	Euphorbia aellenii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3022	Toxicopueraria peduncularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19229	Aniba parviflora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15430	Abutilon grandiflorum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14953	Thapsia transtagana	Species	Apiaceae	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	1
Others	6

Activity Type	# Activity
Cell Line	1
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[558929]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[558929]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	30.5	%	PMID[558929]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	73.1	%	PMID[558929]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	95.9	%	PMID[558929]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	9.4	nM	PMID[558929]
NPT2	Others	Unspecified		Activity	=	1.6	n.a.	PMID[558929]

☑ 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 NPC5046 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	184
0.1-0.2	2489
0.2-0.3	13754
0.3-0.4	11929
0.4-0.5	5134
0.5-0.6	5315
0.6-0.7	2848
0.7-0.8	840
0.8-0.85	116
0.85-0.9	67
0.9-0.95	10
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC49168
1.0	High Similarity	NPC145552
1.0	High Similarity	NPC254509
1.0	High Similarity	NPC196358
0.9855	High Similarity	NPC70982
0.9855	High Similarity	NPC230704
0.9855	High Similarity	NPC200243
0.9853	High Similarity	NPC195489
0.9706	High Similarity	NPC111234
0.9577	High Similarity	NPC331618
0.9577	High Similarity	NPC257191
0.9559	High Similarity	NPC45296
0.9444	High Similarity	NPC472342
0.9444	High Similarity	NPC65897
0.9444	High Similarity	NPC85346
0.9444	High Similarity	NPC302041
0.9429	High Similarity	NPC62657
0.9429	High Similarity	NPC192638
0.9429	High Similarity	NPC25511
0.9296	High Similarity	NPC240235
0.9296	High Similarity	NPC3403
0.9296	High Similarity	NPC178383
0.9296	High Similarity	NPC212879
0.9296	High Similarity	NPC104387
0.9296	High Similarity	NPC185536
0.9296	High Similarity	NPC231256
0.9178	High Similarity	NPC312328
0.9167	High Similarity	NPC93662
0.9167	High Similarity	NPC14112
0.9167	High Similarity	NPC86305
0.9167	High Similarity	NPC78067
0.9167	High Similarity	NPC237460
0.9167	High Similarity	NPC278091
0.9167	High Similarity	NPC91573
0.9155	High Similarity	NPC472503
0.9155	High Similarity	NPC308440
0.9041	High Similarity	NPC202540
0.9041	High Similarity	NPC119355
0.9041	High Similarity	NPC248830
0.9041	High Similarity	NPC212241
0.8919	High Similarity	NPC285761
0.8919	High Similarity	NPC102708
0.8919	High Similarity	NPC6978
0.8919	High Similarity	NPC167037
0.8919	High Similarity	NPC244385
0.8919	High Similarity	NPC31828
0.8919	High Similarity	NPC477819
0.8919	High Similarity	NPC138621
0.8919	High Similarity	NPC42853
0.8919	High Similarity	NPC477817
0.8919	High Similarity	NPC301707
0.8904	High Similarity	NPC189883
0.8831	High Similarity	NPC113978
0.8824	High Similarity	NPC41577
0.8824	High Similarity	NPC473276
0.8824	High Similarity	NPC476737
0.8824	High Similarity	NPC474380
0.8824	High Similarity	NPC27243
0.88	High Similarity	NPC49599
0.88	High Similarity	NPC80297
0.88	High Similarity	NPC116119
0.88	High Similarity	NPC475727
0.88	High Similarity	NPC472742
0.88	High Similarity	NPC273410
0.88	High Similarity	NPC80530
0.88	High Similarity	NPC49627
0.8784	High Similarity	NPC34019
0.8784	High Similarity	NPC260301
0.8784	High Similarity	NPC307336
0.8784	High Similarity	NPC138502
0.8767	High Similarity	NPC257347
0.8767	High Similarity	NPC121744
0.8767	High Similarity	NPC322353
0.8767	High Similarity	NPC103822
0.8767	High Similarity	NPC141071
0.8767	High Similarity	NPC118508
0.8767	High Similarity	NPC471723
0.8684	High Similarity	NPC102253
0.8684	High Similarity	NPC78545
0.8684	High Similarity	NPC13554
0.8684	High Similarity	NPC71535
0.8684	High Similarity	NPC475679
0.8684	High Similarity	NPC322313
0.8684	High Similarity	NPC236237
0.8676	High Similarity	NPC69149
0.8667	High Similarity	NPC472499
0.8667	High Similarity	NPC472500
0.8667	High Similarity	NPC472501
0.8649	High Similarity	NPC73875
0.8649	High Similarity	NPC134330
0.8649	High Similarity	NPC38141
0.8649	High Similarity	NPC46160
0.8649	High Similarity	NPC129165
0.8649	High Similarity	NPC202642
0.8649	High Similarity	NPC300324
0.8649	High Similarity	NPC240604
0.863	High Similarity	NPC476736
0.8611	High Similarity	NPC164045
0.8611	High Similarity	NPC301226
0.8608	High Similarity	NPC76518
0.859	High Similarity	NPC82623
0.859	High Similarity	NPC134481
0.8571	High Similarity	NPC473230
0.8571	High Similarity	NPC475884
0.8553	High Similarity	NPC1319
0.8553	High Similarity	NPC24504
0.8553	High Similarity	NPC476316
0.8533	High Similarity	NPC214570
0.8514	High Similarity	NPC136188
0.8514	High Similarity	NPC22105
0.8514	High Similarity	NPC230301
0.8514	High Similarity	NPC285893
0.8514	High Similarity	NPC162742
0.8514	High Similarity	NPC288035
0.8514	High Similarity	NPC304309
0.8514	High Similarity	NPC134847
0.8514	High Similarity	NPC28657
0.85	High Similarity	NPC71520
0.85	High Similarity	NPC269058
0.8493	Intermediate Similarity	NPC201373
0.8493	Intermediate Similarity	NPC472506
0.8493	Intermediate Similarity	NPC211009
0.8481	Intermediate Similarity	NPC86238
0.8462	Intermediate Similarity	NPC296701
0.8462	Intermediate Similarity	NPC477599
0.8462	Intermediate Similarity	NPC218616
0.8442	Intermediate Similarity	NPC47149
0.8442	Intermediate Similarity	NPC236112
0.8442	Intermediate Similarity	NPC206735
0.8421	Intermediate Similarity	NPC475
0.8421	Intermediate Similarity	NPC275910
0.8421	Intermediate Similarity	NPC205455
0.8421	Intermediate Similarity	NPC186191
0.8421	Intermediate Similarity	NPC472502
0.84	Intermediate Similarity	NPC113733
0.84	Intermediate Similarity	NPC321016
0.84	Intermediate Similarity	NPC321381
0.84	Intermediate Similarity	NPC107059
0.84	Intermediate Similarity	NPC470362
0.8395	Intermediate Similarity	NPC89747
0.8382	Intermediate Similarity	NPC71460
0.8382	Intermediate Similarity	NPC148174
0.8382	Intermediate Similarity	NPC218585
0.8378	Intermediate Similarity	NPC100334
0.8378	Intermediate Similarity	NPC469534
0.8378	Intermediate Similarity	NPC469533
0.8378	Intermediate Similarity	NPC469593
0.8375	Intermediate Similarity	NPC22133
0.8354	Intermediate Similarity	NPC207013
0.8354	Intermediate Similarity	NPC470929
0.8354	Intermediate Similarity	NPC475726
0.8354	Intermediate Similarity	NPC5280
0.8354	Intermediate Similarity	NPC110778
0.8354	Intermediate Similarity	NPC232023
0.8354	Intermediate Similarity	NPC216420
0.8354	Intermediate Similarity	NPC85095
0.8354	Intermediate Similarity	NPC211135
0.8354	Intermediate Similarity	NPC477818
0.8354	Intermediate Similarity	NPC246956
0.8354	Intermediate Similarity	NPC472743
0.8333	Intermediate Similarity	NPC241085
0.8333	Intermediate Similarity	NPC157655
0.8333	Intermediate Similarity	NPC474531
0.8333	Intermediate Similarity	NPC210323
0.8333	Intermediate Similarity	NPC299948
0.8333	Intermediate Similarity	NPC470830
0.8312	Intermediate Similarity	NPC30986
0.8312	Intermediate Similarity	NPC209430
0.8312	Intermediate Similarity	NPC472463
0.8312	Intermediate Similarity	NPC5604
0.8312	Intermediate Similarity	NPC47808
0.8293	Intermediate Similarity	NPC67872
0.8293	Intermediate Similarity	NPC146937
0.8289	Intermediate Similarity	NPC198968
0.8289	Intermediate Similarity	NPC155986
0.8289	Intermediate Similarity	NPC318495
0.8272	Intermediate Similarity	NPC94462
0.8267	Intermediate Similarity	NPC144075
0.8261	Intermediate Similarity	NPC114891
0.825	Intermediate Similarity	NPC74595
0.825	Intermediate Similarity	NPC474482
0.825	Intermediate Similarity	NPC264665
0.825	Intermediate Similarity	NPC255882
0.825	Intermediate Similarity	NPC475745
0.825	Intermediate Similarity	NPC209802
0.8243	Intermediate Similarity	NPC182717
0.8228	Intermediate Similarity	NPC470049
0.8228	Intermediate Similarity	NPC472504
0.8228	Intermediate Similarity	NPC30166
0.8228	Intermediate Similarity	NPC477858
0.8228	Intermediate Similarity	NPC248886
0.8194	Intermediate Similarity	NPC2648
0.8194	Intermediate Similarity	NPC160209
0.8182	Intermediate Similarity	NPC477522
0.8182	Intermediate Similarity	NPC473943
0.8182	Intermediate Similarity	NPC18603
0.8182	Intermediate Similarity	NPC474216
0.8182	Intermediate Similarity	NPC76931
0.8182	Intermediate Similarity	NPC87604
0.8182	Intermediate Similarity	NPC307965

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 NPC5046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2748
0.2-0.3	4377
0.3-0.4	1263
0.4-0.5	218
0.5-0.6	158
0.6-0.7	147
0.7-0.8	38
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD7525	Registered
0.8514	High Similarity	NPD7339	Approved
0.8514	High Similarity	NPD6942	Approved
0.8148	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7645	Phase 2
0.7838	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6924	Approved
0.7662	Intermediate Similarity	NPD6926	Approved
0.7632	Intermediate Similarity	NPD7151	Approved
0.7632	Intermediate Similarity	NPD7152	Approved
0.7632	Intermediate Similarity	NPD7150	Approved
0.7632	Intermediate Similarity	NPD4243	Approved
0.76	Intermediate Similarity	NPD6922	Approved
0.76	Intermediate Similarity	NPD6923	Approved
0.759	Intermediate Similarity	NPD4786	Approved
0.7558	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD4787	Phase 1
0.75	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD7143	Approved
0.747	Intermediate Similarity	NPD4788	Approved
0.7468	Intermediate Similarity	NPD6933	Approved
0.7436	Intermediate Similarity	NPD4785	Approved
0.7436	Intermediate Similarity	NPD4784	Approved
0.7412	Intermediate Similarity	NPD3618	Phase 1
0.7403	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8035	Phase 2
0.7386	Intermediate Similarity	NPD8034	Phase 2
0.7386	Intermediate Similarity	NPD6079	Approved
0.7349	Intermediate Similarity	NPD3667	Approved
0.7317	Intermediate Similarity	NPD4748	Discontinued
0.725	Intermediate Similarity	NPD6117	Approved
0.7215	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6929	Approved
0.716	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4190	Phase 3
0.7125	Intermediate Similarity	NPD5275	Approved
0.7111	Intermediate Similarity	NPD4202	Approved
0.7108	Intermediate Similarity	NPD6930	Phase 2
0.7108	Intermediate Similarity	NPD6931	Approved
0.7108	Intermediate Similarity	NPD7509	Discontinued
0.7073	Intermediate Similarity	NPD6118	Approved
0.7073	Intermediate Similarity	NPD6114	Approved
0.7073	Intermediate Similarity	NPD6697	Approved
0.7073	Intermediate Similarity	NPD6115	Approved
0.7024	Intermediate Similarity	NPD6902	Approved
0.6977	Remote Similarity	NPD3665	Phase 1
0.6977	Remote Similarity	NPD3666	Approved
0.6977	Remote Similarity	NPD3133	Approved
0.6951	Remote Similarity	NPD6925	Approved
0.6951	Remote Similarity	NPD6932	Approved
0.6951	Remote Similarity	NPD5776	Phase 2
0.6915	Remote Similarity	NPD7638	Approved
0.6914	Remote Similarity	NPD3703	Phase 2
0.6882	Remote Similarity	NPD4697	Phase 3
0.6882	Remote Similarity	NPD5222	Approved
0.6882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5221	Approved
0.6867	Remote Similarity	NPD7145	Approved
0.686	Remote Similarity	NPD6695	Phase 3
0.6842	Remote Similarity	NPD7640	Approved
0.6842	Remote Similarity	NPD7639	Approved
0.6835	Remote Similarity	NPD4245	Approved
0.6835	Remote Similarity	NPD4244	Approved
0.6835	Remote Similarity	NPD4789	Approved
0.6813	Remote Similarity	NPD7515	Phase 2
0.6809	Remote Similarity	NPD4755	Approved
0.6809	Remote Similarity	NPD5173	Approved
0.6795	Remote Similarity	NPD5360	Phase 3
0.6795	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4195	Approved
0.6786	Remote Similarity	NPD6683	Phase 2
0.6782	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6399	Phase 3
0.6709	Remote Similarity	NPD3698	Phase 2
0.6706	Remote Similarity	NPD6928	Phase 2
0.6706	Remote Similarity	NPD7514	Phase 3
0.6705	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6629	Remote Similarity	NPD5279	Phase 3
0.6623	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5223	Approved
0.6593	Remote Similarity	NPD4753	Phase 2
0.6591	Remote Similarity	NPD3668	Phase 3
0.6562	Remote Similarity	NPD5290	Discontinued
0.6556	Remote Similarity	NPD7524	Approved
0.6556	Remote Similarity	NPD7750	Discontinued
0.6552	Remote Similarity	NPD4221	Approved
0.6552	Remote Similarity	NPD4223	Phase 3
0.6531	Remote Similarity	NPD5224	Approved
0.6531	Remote Similarity	NPD5226	Approved
0.6531	Remote Similarity	NPD5225	Approved
0.6531	Remote Similarity	NPD4633	Approved
0.6531	Remote Similarity	NPD5211	Phase 2
0.6517	Remote Similarity	NPD5329	Approved
0.6512	Remote Similarity	NPD7332	Phase 2
0.6506	Remote Similarity	NPD8264	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6489	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD3671	Phase 1
0.6465	Remote Similarity	NPD5175	Approved
0.6465	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD5174	Approved
0.6437	Remote Similarity	NPD6898	Phase 1
0.6404	Remote Similarity	NPD4197	Approved
0.64	Remote Similarity	NPD5141	Approved
0.6375	Remote Similarity	NPD6705	Phase 1
0.6373	Remote Similarity	NPD6899	Approved
0.6373	Remote Similarity	NPD7320	Approved
0.6373	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD7632	Discontinued
0.6341	Remote Similarity	NPD4758	Discontinued
0.6337	Remote Similarity	NPD4768	Approved
0.6337	Remote Similarity	NPD4767	Approved
0.6324	Remote Similarity	NPD384	Approved
0.6324	Remote Similarity	NPD385	Approved
0.6311	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6373	Approved
0.6304	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7902	Approved
0.6289	Remote Similarity	NPD6084	Phase 2
0.6289	Remote Similarity	NPD6083	Phase 2
0.6279	Remote Similarity	NPD3617	Approved
0.6277	Remote Similarity	NPD7087	Discontinued
0.6275	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD5697	Approved
0.6264	Remote Similarity	NPD4690	Approved
0.6264	Remote Similarity	NPD7146	Approved
0.6264	Remote Similarity	NPD4138	Approved
0.6264	Remote Similarity	NPD5330	Approved
0.6264	Remote Similarity	NPD4688	Approved
0.6264	Remote Similarity	NPD7521	Approved
0.6264	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4693	Phase 3
0.6264	Remote Similarity	NPD7334	Approved
0.6264	Remote Similarity	NPD6684	Approved
0.6264	Remote Similarity	NPD4689	Approved
0.6264	Remote Similarity	NPD6409	Approved
0.6264	Remote Similarity	NPD5205	Approved
0.6263	Remote Similarity	NPD4159	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD4629	Approved
0.6237	Remote Similarity	NPD6051	Approved
0.6214	Remote Similarity	NPD5168	Approved
0.6214	Remote Similarity	NPD4730	Approved
0.6214	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD4729	Approved
0.6214	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD6650	Approved
0.619	Remote Similarity	NPD6847	Approved
0.619	Remote Similarity	NPD8130	Phase 1
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6617	Approved
0.619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6649	Approved
0.617	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6700	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6145	Remote Similarity	NPD6081	Approved
0.6132	Remote Similarity	NPD8297	Approved
0.6132	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD6903	Approved
0.6129	Remote Similarity	NPD4722	Approved
0.6129	Remote Similarity	NPD4723	Approved
0.6129	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD5737	Approved
0.6125	Remote Similarity	NPD4224	Phase 2
0.6105	Remote Similarity	NPD6703	Approved
0.6105	Remote Similarity	NPD6702	Approved
0.6095	Remote Similarity	NPD5251	Approved
0.6095	Remote Similarity	NPD4634	Approved
0.6095	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5248	Approved
0.6095	Remote Similarity	NPD5135	Approved
0.6095	Remote Similarity	NPD5249	Phase 3
0.6095	Remote Similarity	NPD5169	Approved
0.6095	Remote Similarity	NPD5247	Approved
0.6095	Remote Similarity	NPD5250	Approved
0.6092	Remote Similarity	NPD5364	Discontinued
0.6087	Remote Similarity	NPD5690	Phase 2
0.6087	Remote Similarity	NPD5280	Approved
0.6087	Remote Similarity	NPD4694	Approved
0.6067	Remote Similarity	NPD4692	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