NPASS Compound

Structure

NPC11410 OpenBabel07101718332D 44 48 0 0 1 0 0 0 0 0999 V2000 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5663 3.9874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4242 2.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1123 -1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3438 3.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5139 1.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0017 2.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4888 1.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7470 -2.1137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9977 2.3491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9227 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2954 0.1738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6433 0.4130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 13 16 1 0 0 0 0 14 22 2 0 0 0 0 15 22 1 0 0 0 0 16 26 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 36 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 21 33 1 6 0 0 0 22 31 1 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 6 0 0 0 25 33 1 1 0 0 0 25 34 1 0 0 0 0 26 37 2 0 0 0 0 26 44 1 0 0 0 0 27 32 1 0 0 0 0 27 35 1 6 0 0 0 28 34 1 0 0 0 0 28 38 2 0 0 0 0 29 34 1 1 0 0 0 29 39 1 0 0 0 0 30 35 1 1 0 0 0 30 43 1 0 0 0 0 31 40 2 0 0 0 0 31 43 1 0 0 0 0 32 35 1 0 0 0 0 33 41 1 6 0 0 0 34 42 1 1 0 0 0 35 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.31
Volume:	629.154
LogP:	5.205
LogD:	3.274
LogS:	-4.405
# Rotatable Bonds:	12
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	5.084
Fsp3:	0.629
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.046
MDCK Permeability:	1.752927346387878e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.784
Human Intestinal Absorption (HIA):	0.637
20% Bioavailability (F20%):	0.219
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.319
Plasma Protein Binding (PPB):	92.35779571533203%
Volume Distribution (VD):	1.787
Pgp-substrate:	4.299668788909912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.277
CYP2C19-substrate:	0.155
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.775
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	4.982
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.625
Human Hepatotoxicity (H-HT):	0.902
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.863
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.531
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC11410

Natural Product ID:	NPC11410
*Common Name:**	QXFOVBNLMKQJFC-NNGASTTLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QXFOVBNLMKQJFC-NNGASTTLSA-N
Standard InCHI:	InChI=1S/C35H46O9/c1-6-7-8-9-13-16-26(37)44-35-27(32(35,4)5)24-18-23(19-36)29(39)34(42)25(17-20(2)28(34)38)33(24,41)21(3)30(35)43-31(40)22-14-11-10-12-15-22/h10-12,14-15,17-18,21,24-25,27,29-30,36,39,41-42H,6-9,13,16,19H2,1-5H3/t21-,24+,25+,27-,29-,30-,33-,34-,35-/m1/s1
SMILES:	CCCCCCCC(=O)O[C@]12[C@H]([C@@H]3C=C(CO)[C@H]([C@]4([C@@H](C=C(C)C4=O)[C@]3([C@H](C)[C@H]1OC(=O)c1ccccc1)O)O)O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375488
PubChem CID:	71712659
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO40396	Wikstroemia scytophylla	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33172265]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	IC50	=	17200.0	nM	PMID[521741]
NPT25	Cell Line	MT4	Homo sapiens	CC50	>	164.0	nM	PMID[521742]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC90	=	0.0038	uM	PMID[521741]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	12.8	nM	PMID[521742]

☑ 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 NPC11410 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	331
0.1-0.2	1135
0.2-0.3	2499
0.3-0.4	5171
0.4-0.5	9625
0.5-0.6	10710
0.6-0.7	10812
0.7-0.8	2069
0.8-0.85	236
0.85-0.9	91
0.9-0.95	4
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC469647
0.9793	High Similarity	NPC469648
0.9793	High Similarity	NPC138641
0.9793	High Similarity	NPC22571
0.9793	High Similarity	NPC283875
0.9658	High Similarity	NPC145649
0.9658	High Similarity	NPC233581
0.9589	High Similarity	NPC472398
0.9527	High Similarity	NPC251139
0.9517	High Similarity	NPC132652
0.9172	High Similarity	NPC140021
0.9172	High Similarity	NPC183540
0.9067	High Similarity	NPC471103
0.9067	High Similarity	NPC51602
0.9032	High Similarity	NPC43304
0.9032	High Similarity	NPC477190
0.9032	High Similarity	NPC477188
0.9013	High Similarity	NPC473670
0.9013	High Similarity	NPC21410
0.9	High Similarity	NPC7095
0.8986	High Similarity	NPC127857
0.8954	High Similarity	NPC106895
0.8947	High Similarity	NPC11588
0.8947	High Similarity	NPC229545
0.8947	High Similarity	NPC134685
0.8947	High Similarity	NPC248265
0.894	High Similarity	NPC470153
0.8933	High Similarity	NPC81698
0.8933	High Similarity	NPC60509
0.8933	High Similarity	NPC250046
0.8919	High Similarity	NPC34943
0.8889	High Similarity	NPC26033
0.8889	High Similarity	NPC259144
0.8889	High Similarity	NPC282239
0.8889	High Similarity	NPC114357
0.8889	High Similarity	NPC228204
0.8889	High Similarity	NPC155329
0.8874	High Similarity	NPC165260
0.8874	High Similarity	NPC161239
0.8874	High Similarity	NPC112216
0.8874	High Similarity	NPC198455
0.8861	High Similarity	NPC61891
0.8859	High Similarity	NPC134131
0.8859	High Similarity	NPC25043
0.8854	High Similarity	NPC66193
0.8851	High Similarity	NPC95449
0.8839	High Similarity	NPC49297
0.8824	High Similarity	NPC472030
0.8824	High Similarity	NPC472005
0.8824	High Similarity	NPC265395
0.8824	High Similarity	NPC242262
0.8824	High Similarity	NPC256142
0.8824	High Similarity	NPC249471
0.8824	High Similarity	NPC219419
0.8824	High Similarity	NPC1173
0.8824	High Similarity	NPC304876
0.8824	High Similarity	NPC158333
0.8824	High Similarity	NPC237549
0.8824	High Similarity	NPC472022
0.8824	High Similarity	NPC473414
0.8824	High Similarity	NPC257213
0.8816	High Similarity	NPC197037
0.88	High Similarity	NPC20255
0.88	High Similarity	NPC312393
0.88	High Similarity	NPC240115
0.8784	High Similarity	NPC192658
0.8774	High Similarity	NPC472393
0.8774	High Similarity	NPC181924
0.8766	High Similarity	NPC472549
0.8766	High Similarity	NPC132599
0.8766	High Similarity	NPC112523
0.8766	High Similarity	NPC473632
0.8766	High Similarity	NPC473611
0.8766	High Similarity	NPC469730
0.8766	High Similarity	NPC114410
0.875	High Similarity	NPC470245
0.875	High Similarity	NPC473214
0.875	High Similarity	NPC125033
0.875	High Similarity	NPC91730
0.8742	High Similarity	NPC217918
0.8734	High Similarity	NPC322420
0.8733	High Similarity	NPC311825
0.8733	High Similarity	NPC471107
0.8733	High Similarity	NPC92867
0.8733	High Similarity	NPC471100
0.8733	High Similarity	NPC125882
0.8725	High Similarity	NPC477894
0.8718	High Similarity	NPC471102
0.8716	High Similarity	NPC97947
0.8716	High Similarity	NPC291599
0.8716	High Similarity	NPC87448
0.8716	High Similarity	NPC118080
0.8716	High Similarity	NPC16912
0.8716	High Similarity	NPC27377
0.8716	High Similarity	NPC41481
0.8716	High Similarity	NPC472576
0.871	High Similarity	NPC70344
0.871	High Similarity	NPC217091
0.8701	High Similarity	NPC77719
0.8693	High Similarity	NPC306799
0.8693	High Similarity	NPC101043
0.8684	High Similarity	NPC473215
0.8684	High Similarity	NPC476975
0.8679	High Similarity	NPC471134
0.8675	High Similarity	NPC473602
0.8671	High Similarity	NPC275477
0.8658	High Similarity	NPC182869
0.8658	High Similarity	NPC34012
0.8658	High Similarity	NPC472546
0.8654	High Similarity	NPC469771
0.8649	High Similarity	NPC275592
0.8649	High Similarity	NPC97667
0.8649	High Similarity	NPC162613
0.8649	High Similarity	NPC171207
0.8649	High Similarity	NPC100913
0.8649	High Similarity	NPC90614
0.8649	High Similarity	NPC472547
0.8649	High Similarity	NPC87934
0.8636	High Similarity	NPC472548
0.8636	High Similarity	NPC477905
0.8634	High Similarity	NPC40138
0.8627	High Similarity	NPC254558
0.8618	High Similarity	NPC327031
0.8609	High Similarity	NPC470157
0.8609	High Similarity	NPC184817
0.8609	High Similarity	NPC70403
0.8609	High Similarity	NPC470159
0.8609	High Similarity	NPC96903
0.8609	High Similarity	NPC177940
0.8609	High Similarity	NPC472571
0.8609	High Similarity	NPC200471
0.8609	High Similarity	NPC476973
0.8609	High Similarity	NPC469349
0.8609	High Similarity	NPC472568
0.8609	High Similarity	NPC472575
0.8609	High Similarity	NPC472556
0.8609	High Similarity	NPC471104
0.8609	High Similarity	NPC171525
0.8609	High Similarity	NPC158663
0.8609	High Similarity	NPC473088
0.8609	High Similarity	NPC29704
0.8609	High Similarity	NPC174982
0.8609	High Similarity	NPC472572
0.8581	High Similarity	NPC9905
0.8581	High Similarity	NPC477098
0.8581	High Similarity	NPC477100
0.8581	High Similarity	NPC146310
0.8562	High Similarity	NPC471493
0.8553	High Similarity	NPC475552
0.8553	High Similarity	NPC478263
0.8553	High Similarity	NPC55744
0.8543	High Similarity	NPC188865
0.8543	High Similarity	NPC475759
0.8543	High Similarity	NPC476974
0.8543	High Similarity	NPC25768
0.8543	High Similarity	NPC472570
0.8543	High Similarity	NPC95265
0.8543	High Similarity	NPC472573
0.8543	High Similarity	NPC475122
0.8543	High Similarity	NPC38696
0.8543	High Similarity	NPC11685
0.8543	High Similarity	NPC163719
0.8543	High Similarity	NPC95810
0.8543	High Similarity	NPC241951
0.8543	High Similarity	NPC472569
0.8543	High Similarity	NPC57628
0.8543	High Similarity	NPC70716
0.8543	High Similarity	NPC125106
0.8543	High Similarity	NPC470152
0.8514	High Similarity	NPC39549
0.8509	High Similarity	NPC325732
0.8509	High Similarity	NPC324769
0.8506	High Similarity	NPC477101
0.8506	High Similarity	NPC232583
0.8506	High Similarity	NPC25484
0.8506	High Similarity	NPC477097
0.8506	High Similarity	NPC476173
0.8506	High Similarity	NPC477099
0.85	High Similarity	NPC478073
0.8497	Intermediate Similarity	NPC205389
0.8497	Intermediate Similarity	NPC473760
0.8491	Intermediate Similarity	NPC476077
0.8487	Intermediate Similarity	NPC478264
0.8487	Intermediate Similarity	NPC301946
0.8487	Intermediate Similarity	NPC277053
0.8481	Intermediate Similarity	NPC159692
0.8477	Intermediate Similarity	NPC163087
0.8467	Intermediate Similarity	NPC242355
0.8462	Intermediate Similarity	NPC469477
0.8462	Intermediate Similarity	NPC133430
0.8446	Intermediate Similarity	NPC52523
0.8446	Intermediate Similarity	NPC472551
0.8446	Intermediate Similarity	NPC472545
0.8446	Intermediate Similarity	NPC217673
0.8442	Intermediate Similarity	NPC270590
0.8442	Intermediate Similarity	NPC473403
0.8442	Intermediate Similarity	NPC266265
0.8442	Intermediate Similarity	NPC301556
0.8442	Intermediate Similarity	NPC471101
0.8442	Intermediate Similarity	NPC92293

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 NPC11410 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	779
0.2-0.3	1671
0.3-0.4	2847
0.4-0.5	2235
0.5-0.6	972
0.6-0.7	344
0.7-0.8	28
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
0.8013	Intermediate Similarity	NPD7236	Approved
0.8	Intermediate Similarity	NPD8368	Discontinued
0.7977	Intermediate Similarity	NPD8434	Phase 2
0.7976	Intermediate Similarity	NPD7799	Discontinued
0.7965	Intermediate Similarity	NPD8407	Phase 2
0.7875	Intermediate Similarity	NPD7239	Suspended
0.7816	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8360	Approved
0.7784	Intermediate Similarity	NPD8361	Approved
0.7684	Intermediate Similarity	NPD8435	Approved
0.7616	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8485	Approved
0.7472	Intermediate Similarity	NPD8150	Discontinued
0.744	Intermediate Similarity	NPD7057	Phase 3
0.744	Intermediate Similarity	NPD7058	Phase 2
0.7405	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2629	Approved
0.7308	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7193	Intermediate Similarity	NPD7075	Discontinued
0.7178	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7134	Intermediate Similarity	NPD7961	Discontinued
0.7118	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5402	Approved
0.7059	Intermediate Similarity	NPD6801	Discontinued
0.7018	Intermediate Similarity	NPD5760	Phase 2
0.7018	Intermediate Similarity	NPD5761	Phase 2
0.7018	Intermediate Similarity	NPD7819	Suspended
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD7741	Discontinued
0.7	Intermediate Similarity	NPD7685	Pre-registration
0.699	Remote Similarity	NPD8462	Phase 1
0.6971	Remote Similarity	NPD8127	Discontinued
0.6944	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4380	Phase 2
0.6935	Remote Similarity	NPD8404	Phase 2
0.6931	Remote Similarity	NPD7700	Phase 2
0.6931	Remote Similarity	NPD7699	Phase 2
0.6923	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD8312	Approved
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4198	Discontinued
0.6909	Remote Similarity	NPD8166	Discontinued
0.6906	Remote Similarity	NPD6764	Approved
0.6906	Remote Similarity	NPD6765	Approved
0.6891	Remote Similarity	NPD8320	Phase 1
0.6891	Remote Similarity	NPD8319	Approved
0.6886	Remote Similarity	NPD6799	Approved
0.6879	Remote Similarity	NPD3817	Phase 2
0.6864	Remote Similarity	NPD5403	Approved
0.6862	Remote Similarity	NPD6534	Approved
0.6862	Remote Similarity	NPD6535	Approved
0.6846	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2532	Approved
0.6845	Remote Similarity	NPD2534	Approved
0.6845	Remote Similarity	NPD2533	Approved
0.6839	Remote Similarity	NPD7435	Discontinued
0.6839	Remote Similarity	NPD3882	Suspended
0.6836	Remote Similarity	NPD6232	Discontinued
0.6833	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5844	Phase 1
0.6803	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7008	Discontinued
0.6784	Remote Similarity	NPD3226	Approved
0.6778	Remote Similarity	NPD3751	Discontinued
0.6778	Remote Similarity	NPD3818	Discontinued
0.6776	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD37	Approved
0.6761	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6166	Phase 2
0.676	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6785	Approved
0.6757	Remote Similarity	NPD6784	Approved
0.675	Remote Similarity	NPD3764	Approved
0.6746	Remote Similarity	NPD5401	Approved
0.6743	Remote Similarity	NPD4967	Phase 2
0.6743	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4965	Approved
0.6743	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD230	Phase 1
0.6727	Remote Similarity	NPD5762	Approved
0.6727	Remote Similarity	NPD5763	Approved
0.6724	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5494	Approved
0.6721	Remote Similarity	NPD6559	Discontinued
0.6717	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7874	Approved
0.6709	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6085	Phase 2
0.6707	Remote Similarity	NPD2799	Discontinued
0.6706	Remote Similarity	NPD6273	Approved
0.6705	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7458	Discontinued
0.6685	Remote Similarity	NPD7808	Phase 3
0.6684	Remote Similarity	NPD6779	Approved
0.6684	Remote Similarity	NPD6781	Approved
0.6684	Remote Similarity	NPD6776	Approved
0.6684	Remote Similarity	NPD6780	Approved
0.6684	Remote Similarity	NPD6777	Approved
0.6684	Remote Similarity	NPD6778	Approved
0.6684	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3787	Discontinued
0.6647	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7870	Phase 2
0.6633	Remote Similarity	NPD7871	Phase 2
0.663	Remote Similarity	NPD7251	Discontinued
0.6629	Remote Similarity	NPD2801	Approved
0.6627	Remote Similarity	NPD2346	Discontinued
0.6626	Remote Similarity	NPD6355	Discontinued
0.6623	Remote Similarity	NPD5951	Approved
0.6622	Remote Similarity	NPD6371	Approved
0.6616	Remote Similarity	NPD7701	Phase 2
0.6612	Remote Similarity	NPD7074	Phase 3
0.6609	Remote Similarity	NPD7411	Suspended
0.6607	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2575	Approved
0.6607	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7305	Phase 1
0.66	Remote Similarity	NPD7801	Approved
0.6593	Remote Similarity	NPD7228	Approved
0.659	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5125	Phase 3
0.6581	Remote Similarity	NPD5126	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6577	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD6797	Phase 2
0.6557	Remote Similarity	NPD7054	Approved
0.6554	Remote Similarity	NPD7768	Phase 2
0.6552	Remote Similarity	NPD6647	Phase 2
0.655	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3300	Phase 2
0.6527	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7472	Approved
0.651	Remote Similarity	NPD2067	Discontinued
0.6507	Remote Similarity	NPD1237	Approved
0.6503	Remote Similarity	NPD6663	Approved
0.6497	Remote Similarity	NPD4807	Approved
0.6497	Remote Similarity	NPD4806	Approved
0.6497	Remote Similarity	NPD6287	Discontinued
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5306	Approved
0.6474	Remote Similarity	NPD5305	Approved
0.6463	Remote Similarity	NPD5048	Discontinued
0.646	Remote Similarity	NPD5736	Approved
0.6453	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6319	Approved
0.6452	Remote Similarity	NPD9545	Approved
0.645	Remote Similarity	NPD2800	Approved
0.6447	Remote Similarity	NPD6823	Phase 2
0.6442	Remote Similarity	NPD2313	Discontinued
0.6432	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6004	Phase 3
0.6429	Remote Similarity	NPD7266	Discontinued
0.6429	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6002	Phase 3
0.6429	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6005	Phase 3
0.6425	Remote Similarity	NPD3749	Approved
0.6418	Remote Similarity	NPD8151	Discontinued
0.6416	Remote Similarity	NPD1512	Approved
0.6416	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7003	Approved
0.6412	Remote Similarity	NPD3750	Approved
0.6409	Remote Similarity	NPD6959	Discontinued
0.6409	Remote Similarity	NPD7199	Phase 2
0.6407	Remote Similarity	NPD7033	Discontinued
0.6407	Remote Similarity	NPD1510	Phase 2
0.64	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5647	Approved
0.6395	Remote Similarity	NPD164	Approved
0.6394	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1549	Phase 2
0.6389	Remote Similarity	NPD919	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