NPASS Compound

Structure

CID302041 OpenBabel06191716112D 30 34 0 0 1 0 0 0 0 0999 V2000 -4.3942 5.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9999 4.8986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8840 3.1619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6905 -2.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 -1.0085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7912 3.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7448 3.7691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4897 2.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 -1.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5343 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3793 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6897 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8455 1.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8450 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0463 4.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5361 2.4373 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6902 -1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5358 1.4624 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8455 -1.4635 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5346 -1.4630 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8450 -0.4882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6905 0.9748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6903 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8453 -0.4877 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 3.4009 -1.9627 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 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 20 3 1 1 0 0 0 20 22 1 0 0 0 0 21 4 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 6 0 0 0 23 28 1 6 0 0 0 24 30 1 6 0 0 0 25 27 1 1 0 0 0 25 29 1 0 0 0 0 26 27 1 6 0 0 0 27 6 1 1 0 0 0 28 29 1 1 0 0 0 29 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.37
Volume:	473.512
LogP:	8.125
LogD:	5.793
LogS:	-6.688
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	5.512
Fsp3:	0.931
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:	-4.838
MDCK Permeability:	1.1164252100570593e-05
Pgp-inhibitor:	0.131
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	92.06375885009766%
Volume Distribution (VD):	1.923
Pgp-substrate:	1.3710896968841553%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.245
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.144
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.669

ADMET: Excretion

Clearance (CL):	16.748
Half-life (T1/2):	0.031

ADMET: Toxicity

hERG Blockers:	0.967
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.605
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.961
Carcinogencity:	0.234
Eye Corrosion:	0.795
Eye Irritation:	0.431
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC302041

Natural Product ID:	NPC302041
*Common Name:**	XZEUYTKSAYNYPK-WXPWFURYSA-N
IUPAC Name:	n.a.
Synonyms:	29-Nor-Cycloartenol
Standard InCHIKey:	XZEUYTKSAYNYPK-WXPWFURYSA-N
Standard InCHI:	InChI=1S/C29H48O/c1-19(2)8-7-9-20(3)22-12-14-27(6)25-11-10-23-21(4)24(30)13-15-28(23)18-29(25,28)17-16-26(22,27)5/h8,20-25,30H,7,9-18H2,1-6H3/t20-,21+,22-,23+,24+,25+,26-,27+,28-,29+/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL441883
PubChem CID:	14524546
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
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6988	Diploschistes cretaceus	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6815	Streptomyces sclerotialus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8037	Bryum rutilans	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6429	Phlomis regelii	Species	Lamiaceae	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[536536]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[536536]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	30.2	%	PMID[536536]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	71.4	%	PMID[536536]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	94.6	%	PMID[536536]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	9.5	nM	PMID[536536]
NPT2	Others	Unspecified		Activity	=	1.8	n.a.	PMID[536536]

☑ 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 NPC302041 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	1717
0.2-0.3	9128
0.3-0.4	15407
0.4-0.5	5982
0.5-0.6	5395
0.6-0.7	3561
0.7-0.8	1030
0.8-0.85	200
0.85-0.9	58
0.9-0.95	32
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65897
1.0	High Similarity	NPC85346
0.9726	High Similarity	NPC312328
0.9722	High Similarity	NPC237460
0.9459	High Similarity	NPC285761
0.9459	High Similarity	NPC244385
0.9459	High Similarity	NPC138621
0.9459	High Similarity	NPC6978
0.9459	High Similarity	NPC167037
0.9452	High Similarity	NPC189883
0.9444	High Similarity	NPC5046
0.9444	High Similarity	NPC196358
0.9444	High Similarity	NPC145552
0.9444	High Similarity	NPC254509
0.9444	High Similarity	NPC49168
0.9351	High Similarity	NPC113978
0.9333	High Similarity	NPC80530
0.9333	High Similarity	NPC273410
0.9324	High Similarity	NPC34019
0.9315	High Similarity	NPC257347
0.9315	High Similarity	NPC141071
0.9315	High Similarity	NPC230704
0.9315	High Similarity	NPC200243
0.9315	High Similarity	NPC471723
0.9315	High Similarity	NPC70982
0.9306	High Similarity	NPC195489
0.9211	High Similarity	NPC322313
0.9211	High Similarity	NPC102253
0.9211	High Similarity	NPC236237
0.9211	High Similarity	NPC13554
0.9189	High Similarity	NPC129165
0.9189	High Similarity	NPC202642
0.9189	High Similarity	NPC46160
0.9189	High Similarity	NPC240604
0.9189	High Similarity	NPC134330
0.9189	High Similarity	NPC300324
0.9167	High Similarity	NPC111234
0.9103	High Similarity	NPC82623
0.9103	High Similarity	NPC134481
0.9079	High Similarity	NPC1319
0.9067	High Similarity	NPC331618
0.9067	High Similarity	NPC257191
0.9067	High Similarity	NPC214570
0.9054	High Similarity	NPC136188
0.9054	High Similarity	NPC134847
0.9054	High Similarity	NPC285893
0.9054	High Similarity	NPC118508
0.9054	High Similarity	NPC322353
0.9054	High Similarity	NPC22105
0.9054	High Similarity	NPC230301
0.9054	High Similarity	NPC121744
0.9054	High Similarity	NPC304309
0.9054	High Similarity	NPC28657
0.9054	High Similarity	NPC288035
0.9054	High Similarity	NPC162742
0.9028	High Similarity	NPC45296
0.9	High Similarity	NPC71520
0.9	High Similarity	NPC269058
0.8974	High Similarity	NPC296701
0.8974	High Similarity	NPC218616
0.8961	High Similarity	NPC236112
0.8947	High Similarity	NPC472342
0.8947	High Similarity	NPC275910
0.8947	High Similarity	NPC186191
0.8947	High Similarity	NPC205455
0.8933	High Similarity	NPC321381
0.8933	High Similarity	NPC107059
0.8933	High Similarity	NPC73875
0.8933	High Similarity	NPC113733
0.8933	High Similarity	NPC321016
0.8933	High Similarity	NPC470362
0.8919	High Similarity	NPC100334
0.8919	High Similarity	NPC192638
0.8919	High Similarity	NPC62657
0.8919	High Similarity	NPC25511
0.8889	High Similarity	NPC89747
0.8875	High Similarity	NPC22133
0.8861	High Similarity	NPC110778
0.8861	High Similarity	NPC207013
0.8861	High Similarity	NPC477818
0.8846	High Similarity	NPC474531
0.8831	High Similarity	NPC30986
0.8831	High Similarity	NPC472463
0.8831	High Similarity	NPC209430
0.8816	High Similarity	NPC318495
0.8816	High Similarity	NPC155986
0.8816	High Similarity	NPC198968
0.88	High Similarity	NPC212879
0.88	High Similarity	NPC104387
0.88	High Similarity	NPC3403
0.88	High Similarity	NPC185536
0.88	High Similarity	NPC240235
0.88	High Similarity	NPC231256
0.88	High Similarity	NPC178383
0.8784	High Similarity	NPC201373
0.8784	High Similarity	NPC182717
0.878	High Similarity	NPC67872
0.8765	High Similarity	NPC94462
0.875	High Similarity	NPC209802
0.875	High Similarity	NPC160209
0.8734	High Similarity	NPC470049
0.8734	High Similarity	NPC30166
0.8734	High Similarity	NPC248886
0.8701	High Similarity	NPC18603
0.8701	High Similarity	NPC318136
0.8701	High Similarity	NPC474216
0.8701	High Similarity	NPC477522
0.8701	High Similarity	NPC76931
0.8701	High Similarity	NPC87604
0.8701	High Similarity	NPC307965
0.8701	High Similarity	NPC473943
0.8684	High Similarity	NPC93662
0.8684	High Similarity	NPC91573
0.8684	High Similarity	NPC247325
0.8684	High Similarity	NPC290598
0.8684	High Similarity	NPC78067
0.8684	High Similarity	NPC27765
0.8684	High Similarity	NPC244488
0.8684	High Similarity	NPC265328
0.8684	High Similarity	NPC86305
0.8684	High Similarity	NPC120098
0.8684	High Similarity	NPC122418
0.8684	High Similarity	NPC14112
0.8684	High Similarity	NPC278091
0.8684	High Similarity	NPC30590
0.8667	High Similarity	NPC469534
0.8667	High Similarity	NPC472503
0.8667	High Similarity	NPC308440
0.8667	High Similarity	NPC469533
0.8667	High Similarity	NPC469593
0.8649	High Similarity	NPC167706
0.8625	High Similarity	NPC470558
0.8625	High Similarity	NPC141941
0.8625	High Similarity	NPC193870
0.8608	High Similarity	NPC470383
0.859	High Similarity	NPC84694
0.859	High Similarity	NPC47982
0.859	High Similarity	NPC143182
0.859	High Similarity	NPC28862
0.859	High Similarity	NPC328714
0.859	High Similarity	NPC81306
0.859	High Similarity	NPC109546
0.8571	High Similarity	NPC119355
0.8571	High Similarity	NPC470758
0.8571	High Similarity	NPC248830
0.8571	High Similarity	NPC34177
0.8571	High Similarity	NPC101475
0.8571	High Similarity	NPC202540
0.8571	High Similarity	NPC90979
0.8571	High Similarity	NPC40394
0.8571	High Similarity	NPC470711
0.8571	High Similarity	NPC472805
0.8571	High Similarity	NPC212241
0.8571	High Similarity	NPC157996
0.8553	High Similarity	NPC34700
0.8553	High Similarity	NPC103822
0.8553	High Similarity	NPC138374
0.8537	High Similarity	NPC125399
0.8537	High Similarity	NPC24277
0.8537	High Similarity	NPC201273
0.8533	High Similarity	NPC474140
0.8519	High Similarity	NPC478102
0.8519	High Similarity	NPC474493
0.8519	High Similarity	NPC124172
0.8519	High Similarity	NPC474047
0.8519	High Similarity	NPC475798
0.8519	High Similarity	NPC470077
0.8519	High Similarity	NPC127606
0.85	High Similarity	NPC87489
0.85	High Similarity	NPC20853
0.85	High Similarity	NPC201852
0.85	High Similarity	NPC49964
0.85	High Similarity	NPC101462
0.85	High Similarity	NPC202389
0.8493	Intermediate Similarity	NPC94192
0.8481	Intermediate Similarity	NPC164840
0.8481	Intermediate Similarity	NPC241290
0.8481	Intermediate Similarity	NPC209944
0.8481	Intermediate Similarity	NPC234193
0.8481	Intermediate Similarity	NPC26117
0.8471	Intermediate Similarity	NPC110923
0.8471	Intermediate Similarity	NPC74296
0.8462	Intermediate Similarity	NPC99168
0.8462	Intermediate Similarity	NPC31828
0.8462	Intermediate Similarity	NPC253807
0.8462	Intermediate Similarity	NPC230295
0.8462	Intermediate Similarity	NPC470396
0.8462	Intermediate Similarity	NPC158662
0.8462	Intermediate Similarity	NPC300499
0.8462	Intermediate Similarity	NPC301707
0.8462	Intermediate Similarity	NPC102708
0.8462	Intermediate Similarity	NPC196753
0.8462	Intermediate Similarity	NPC11908
0.8462	Intermediate Similarity	NPC42853
0.8462	Intermediate Similarity	NPC98386
0.8462	Intermediate Similarity	NPC477514
0.8462	Intermediate Similarity	NPC474989
0.8462	Intermediate Similarity	NPC477819
0.8462	Intermediate Similarity	NPC22955
0.8462	Intermediate Similarity	NPC477817

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 NPC302041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1874
0.2-0.3	4595
0.3-0.4	1760
0.4-0.5	342
0.5-0.6	157
0.6-0.7	178
0.7-0.8	52
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD7525	Registered
0.9054	High Similarity	NPD7339	Approved
0.9054	High Similarity	NPD6942	Approved
0.8442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7645	Phase 2
0.8182	Intermediate Similarity	NPD6926	Approved
0.8182	Intermediate Similarity	NPD6924	Approved
0.8158	Intermediate Similarity	NPD7151	Approved
0.8158	Intermediate Similarity	NPD4243	Approved
0.8158	Intermediate Similarity	NPD7152	Approved
0.8158	Intermediate Similarity	NPD7150	Approved
0.8133	Intermediate Similarity	NPD6923	Approved
0.8133	Intermediate Similarity	NPD6922	Approved
0.8072	Intermediate Similarity	NPD4786	Approved
0.8026	Intermediate Similarity	NPD7143	Approved
0.8026	Intermediate Similarity	NPD7144	Approved
0.8023	Intermediate Similarity	NPD5328	Approved
0.7975	Intermediate Similarity	NPD6933	Approved
0.7949	Intermediate Similarity	NPD4785	Approved
0.7949	Intermediate Similarity	NPD4784	Approved
0.7882	Intermediate Similarity	NPD3618	Phase 1
0.7841	Intermediate Similarity	NPD6079	Approved
0.7831	Intermediate Similarity	NPD3667	Approved
0.7765	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6929	Approved
0.7625	Intermediate Similarity	NPD4190	Phase 3
0.7625	Intermediate Similarity	NPD5275	Approved
0.759	Intermediate Similarity	NPD6930	Phase 2
0.759	Intermediate Similarity	NPD7509	Discontinued
0.759	Intermediate Similarity	NPD4748	Discontinued
0.759	Intermediate Similarity	NPD6931	Approved
0.7586	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD6902	Approved
0.7442	Intermediate Similarity	NPD3666	Approved
0.7442	Intermediate Similarity	NPD3665	Phase 1
0.7442	Intermediate Similarity	NPD3133	Approved
0.7439	Intermediate Similarity	NPD6925	Approved
0.7439	Intermediate Similarity	NPD5776	Phase 2
0.7439	Intermediate Similarity	NPD6932	Approved
0.7436	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7145	Approved
0.734	Intermediate Similarity	NPD7638	Approved
0.7326	Intermediate Similarity	NPD6695	Phase 3
0.7312	Intermediate Similarity	NPD5222	Approved
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD4697	Phase 3
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7639	Approved
0.7263	Intermediate Similarity	NPD7640	Approved
0.7262	Intermediate Similarity	NPD4195	Approved
0.7262	Intermediate Similarity	NPD6683	Phase 2
0.7253	Intermediate Similarity	NPD7515	Phase 2
0.7241	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4755	Approved
0.7234	Intermediate Similarity	NPD5173	Approved
0.7176	Intermediate Similarity	NPD7514	Phase 3
0.7174	Intermediate Similarity	NPD6399	Phase 3
0.7159	Intermediate Similarity	NPD6893	Approved
0.7143	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4788	Approved
0.7125	Intermediate Similarity	NPD4787	Phase 1
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7079	Intermediate Similarity	NPD5279	Phase 3
0.7065	Intermediate Similarity	NPD8035	Phase 2
0.7065	Intermediate Similarity	NPD8034	Phase 2
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7037	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4753	Phase 2
0.7011	Intermediate Similarity	NPD4223	Phase 3
0.7011	Intermediate Similarity	NPD4221	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD7750	Discontinued
0.7	Intermediate Similarity	NPD7524	Approved
0.6988	Remote Similarity	NPD8264	Approved
0.6979	Remote Similarity	NPD5290	Discontinued
0.6977	Remote Similarity	NPD7332	Phase 2
0.6966	Remote Similarity	NPD5329	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6939	Remote Similarity	NPD5224	Approved
0.6915	Remote Similarity	NPD7748	Approved
0.6905	Remote Similarity	NPD6117	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6897	Remote Similarity	NPD6898	Phase 1
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6867	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4197	Approved
0.6824	Remote Similarity	NPD6116	Phase 1
0.68	Remote Similarity	NPD5141	Approved
0.679	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6744	Remote Similarity	NPD6114	Approved
0.6744	Remote Similarity	NPD6697	Approved
0.6744	Remote Similarity	NPD6115	Approved
0.6744	Remote Similarity	NPD6118	Approved
0.6739	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4768	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6703	Remote Similarity	NPD6684	Approved
0.6703	Remote Similarity	NPD4689	Approved
0.6703	Remote Similarity	NPD4693	Phase 3
0.6703	Remote Similarity	NPD4688	Approved
0.6703	Remote Similarity	NPD5205	Approved
0.6703	Remote Similarity	NPD4690	Approved
0.6703	Remote Similarity	NPD7521	Approved
0.6703	Remote Similarity	NPD7334	Approved
0.6703	Remote Similarity	NPD6409	Approved
0.6703	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7146	Approved
0.6703	Remote Similarity	NPD5330	Approved
0.6703	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD7087	Discontinued
0.6701	Remote Similarity	NPD7902	Approved
0.6701	Remote Similarity	NPD6083	Phase 2
0.6701	Remote Similarity	NPD6084	Phase 2
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6051	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.66	Remote Similarity	NPD7632	Discontinued
0.6588	Remote Similarity	NPD3703	Phase 2
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6617	Approved
0.6559	Remote Similarity	NPD4722	Approved
0.6559	Remote Similarity	NPD6903	Approved
0.6559	Remote Similarity	NPD5737	Approved
0.6559	Remote Similarity	NPD4723	Approved
0.6559	Remote Similarity	NPD6672	Approved
0.6552	Remote Similarity	NPD3617	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6522	Remote Similarity	NPD5280	Approved
0.6522	Remote Similarity	NPD5690	Phase 2
0.6522	Remote Similarity	NPD4694	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6509	Remote Similarity	NPD8297	Approved
0.6506	Remote Similarity	NPD4789	Approved
0.6506	Remote Similarity	NPD4244	Approved
0.6506	Remote Similarity	NPD4245	Approved
0.65	Remote Similarity	NPD4159	Approved
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5135	Approved
0.6476	Remote Similarity	NPD5249	Phase 3
0.6463	Remote Similarity	NPD5360	Phase 3
0.6463	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD5215	Approved
0.6415	Remote Similarity	NPD5216	Approved
0.6415	Remote Similarity	NPD5217	Approved
0.6415	Remote Similarity	NPD5127	Approved
0.6404	Remote Similarity	NPD6928	Phase 2
0.6392	Remote Similarity	NPD6001	Approved
0.6392	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7900	Approved
0.6386	Remote Similarity	NPD3698	Phase 2
0.6364	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD7327	Approved
0.6354	Remote Similarity	NPD7637	Suspended
0.6344	Remote Similarity	NPD6098	Approved
0.6333	Remote Similarity	NPD4692	Approved
0.6333	Remote Similarity	NPD4139	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