NPASS Compound

Structure

NPC475336 OpenBabel07101719512D 57 62 0 0 1 0 0 0 0 0999 V2000 -7.7196 -2.6035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2525 -1.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0944 0.5544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8289 3.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4796 3.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5629 3.2496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2476 0.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8654 -2.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3279 -5.2892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2091 3.0543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1821 -4.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5944 -4.7264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8552 2.2001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6462 3.7878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3028 -4.0188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7151 -3.8097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9386 2.0794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7295 3.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8007 -1.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0947 1.3991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9246 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1318 -2.3945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4530 1.2203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0682 2.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5693 -3.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3757 2.8130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7308 0.9826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6014 -0.9246 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9246 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7175 1.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6899 -2.5393 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9568 1.0400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9564 -1.9764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8007 0.4623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4945 0.2393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5614 1.3554 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2777 -2.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4591 2.6923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0771 -1.0597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9168 2.3954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6014 -0.0000 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 -1.0237 2.1561 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5441 -2.1854 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9613 1.9613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4021 -1.3869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8734 0.9193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1022 -2.3302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0573 -0.4942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1570 -3.6649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8962 3.4258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9313 -0.7059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6948 3.0202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9246 -0.9246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6101 0.0659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1052 1.8381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2393 0.8931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 40 1 0 0 0 0 6 40 1 0 0 0 0 8 22 2 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 25 2 0 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 18 26 1 0 0 0 0 19 28 1 0 0 0 0 19 29 1 0 0 0 0 20 27 1 0 0 0 0 20 43 1 0 0 0 0 21 42 1 0 0 0 0 21 54 1 0 0 0 0 22 37 1 0 0 0 0 23 27 1 0 0 0 0 23 30 2 0 0 0 0 24 45 2 0 0 0 0 24 57 1 0 0 0 0 25 31 1 0 0 0 0 26 38 1 0 0 0 0 27 55 1 6 0 0 0 28 41 1 1 0 0 0 28 46 1 0 0 0 0 29 42 1 6 0 0 0 29 54 1 0 0 0 0 30 32 1 0 0 0 0 30 40 1 0 0 0 0 31 33 1 0 0 0 0 31 44 1 6 0 0 0 32 35 1 0 0 0 0 32 47 1 6 0 0 0 33 39 1 0 0 0 0 33 48 1 6 0 0 0 34 36 1 0 0 0 0 34 41 1 6 0 0 0 34 42 1 0 0 0 0 35 41 1 0 0 0 0 35 49 2 0 0 0 0 36 43 1 1 0 0 0 36 56 1 0 0 0 0 37 44 2 3 0 0 0 37 50 1 0 0 0 0 38 51 2 0 0 0 0 38 56 1 0 0 0 0 39 52 2 0 0 0 0 39 55 1 0 0 0 0 40 43 1 0 0 0 0 41 7 1 6 0 0 0 42 57 1 1 0 0 0 43 53 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	789.34
Volume:	791.941
LogP:	3.457
LogD:	2.49
LogS:	-4.658
# Rotatable Bonds:	13
TPSA:	212.39
# H-Bond Aceptor:	14
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	6.359
Fsp3:	0.558
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.386
MDCK Permeability:	6.153735012048855e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	94.70499420166016%
Volume Distribution (VD):	1.413
Pgp-substrate:	4.449990272521973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.546
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	3.635
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.64
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.058
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC475336

Natural Product ID:	NPC475336
*Common Name:**	ADDGUHVEJPNWQZ-WLNUZSSLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ADDGUHVEJPNWQZ-WLNUZSSLSA-N
Standard InCHI:	InChI=1S/C43H51NO13/c1-8-22(2)37(50)44-31(25-15-11-9-12-16-25)33(48)39(52)55-27-20-43(53)36(56-38(51)26-17-13-10-14-18-26)34-41(7,35(49)32(47)30(23(27)3)40(43,5)6)28(46)19-29-42(34,21-54-29)57-24(4)45/h8-18,27-29,31-34,36,46-48,53H,19-21H2,1-7H3,(H,44,50)/b22-8+/t27-,28+,29+,31-,32+,33+,34-,36-,41+,42-,43+/m0/s1
SMILES:	CC=C(C)C(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)O)C)OC(=O)C6=CC=CC=C6)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503720
PubChem CID:	14758690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.6	10'-2 ug/ml	PMID[491628]

☑ 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 NPC475336 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	255
0.1-0.2	1010
0.2-0.3	2483
0.3-0.4	7003
0.4-0.5	12982
0.5-0.6	13611
0.6-0.7	4981
0.7-0.8	311
0.8-0.85	13
0.85-0.9	0
0.9-0.95	14
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC453583
1.0	High Similarity	NPC473300
0.9941	High Similarity	NPC33372
0.9941	High Similarity	NPC67246
0.9882	High Similarity	NPC317882
0.9882	High Similarity	NPC471754
0.9769	High Similarity	NPC321072
0.9769	High Similarity	NPC191193
0.9769	High Similarity	NPC242662
0.9769	High Similarity	NPC215892
0.9766	High Similarity	NPC206211
0.9766	High Similarity	NPC275170
0.9766	High Similarity	NPC473400
0.9766	High Similarity	NPC471629
0.9766	High Similarity	NPC324251
0.9766	High Similarity	NPC306001
0.9713	High Similarity	NPC471606
0.9713	High Similarity	NPC181964
0.9713	High Similarity	NPC208553
0.9657	High Similarity	NPC473558
0.9593	High Similarity	NPC471623
0.9548	High Similarity	NPC472392
0.9545	High Similarity	NPC473490
0.9494	High Similarity	NPC472391
0.9438	High Similarity	NPC472375
0.9422	High Similarity	NPC327699
0.9389	High Similarity	NPC289383
0.9337	High Similarity	NPC116862
0.9056	High Similarity	NPC36607
0.8462	Intermediate Similarity	NPC134685
0.8462	Intermediate Similarity	NPC11588
0.8462	Intermediate Similarity	NPC229545
0.8462	Intermediate Similarity	NPC248265
0.8412	Intermediate Similarity	NPC259144
0.8412	Intermediate Similarity	NPC114357
0.8412	Intermediate Similarity	NPC155329
0.8353	Intermediate Similarity	NPC219419
0.8343	Intermediate Similarity	NPC197037
0.8284	Intermediate Similarity	NPC91730
0.8239	Intermediate Similarity	NPC471493
0.8208	Intermediate Similarity	NPC472393
0.8198	Intermediate Similarity	NPC473670
0.8198	Intermediate Similarity	NPC228204
0.8198	Intermediate Similarity	NPC26033
0.8198	Intermediate Similarity	NPC21410
0.8176	Intermediate Similarity	NPC7095
0.8166	Intermediate Similarity	NPC217918
0.815	Intermediate Similarity	NPC217091
0.815	Intermediate Similarity	NPC106895
0.814	Intermediate Similarity	NPC472005
0.814	Intermediate Similarity	NPC249471
0.814	Intermediate Similarity	NPC304876
0.814	Intermediate Similarity	NPC257213
0.814	Intermediate Similarity	NPC256142
0.814	Intermediate Similarity	NPC473414
0.814	Intermediate Similarity	NPC265395
0.814	Intermediate Similarity	NPC472030
0.814	Intermediate Similarity	NPC242262
0.814	Intermediate Similarity	NPC1173
0.814	Intermediate Similarity	NPC237549
0.814	Intermediate Similarity	NPC158333
0.814	Intermediate Similarity	NPC472022
0.8118	Intermediate Similarity	NPC60509
0.8118	Intermediate Similarity	NPC81698
0.8118	Intermediate Similarity	NPC250046
0.8092	Intermediate Similarity	NPC472549
0.8092	Intermediate Similarity	NPC112523
0.8092	Intermediate Similarity	NPC114410
0.8092	Intermediate Similarity	NPC282239
0.807	Intermediate Similarity	NPC161239
0.807	Intermediate Similarity	NPC198455
0.807	Intermediate Similarity	NPC112216
0.807	Intermediate Similarity	NPC165260
0.8047	Intermediate Similarity	NPC127857
0.8035	Intermediate Similarity	NPC77719
0.8023	Intermediate Similarity	NPC471103
0.8023	Intermediate Similarity	NPC101043
0.8023	Intermediate Similarity	NPC470153
0.8023	Intermediate Similarity	NPC306799
0.8023	Intermediate Similarity	NPC51602
0.8	Intermediate Similarity	NPC469771
0.7989	Intermediate Similarity	NPC469730
0.7989	Intermediate Similarity	NPC473611
0.7989	Intermediate Similarity	NPC473632
0.7989	Intermediate Similarity	NPC132599
0.7988	Intermediate Similarity	NPC38696
0.7977	Intermediate Similarity	NPC472548
0.7955	Intermediate Similarity	NPC471102
0.7895	Intermediate Similarity	NPC474935
0.7874	Intermediate Similarity	NPC477905
0.787	Intermediate Similarity	NPC34012
0.7865	Intermediate Similarity	NPC476077
0.7861	Intermediate Similarity	NPC470245
0.7861	Intermediate Similarity	NPC473214
0.7861	Intermediate Similarity	NPC254558
0.7803	Intermediate Similarity	NPC473215
0.7803	Intermediate Similarity	NPC476975
0.7765	Intermediate Similarity	NPC182869
0.7753	Intermediate Similarity	NPC469399
0.774	Intermediate Similarity	NPC11410
0.7735	Intermediate Similarity	NPC471134
0.7733	Intermediate Similarity	NPC277053
0.7733	Intermediate Similarity	NPC158663
0.7733	Intermediate Similarity	NPC470159
0.7733	Intermediate Similarity	NPC70403
0.7733	Intermediate Similarity	NPC200471
0.7733	Intermediate Similarity	NPC473088
0.7733	Intermediate Similarity	NPC184817
0.7733	Intermediate Similarity	NPC472571
0.7733	Intermediate Similarity	NPC470157
0.7733	Intermediate Similarity	NPC174982
0.7733	Intermediate Similarity	NPC171525
0.7733	Intermediate Similarity	NPC29704
0.7733	Intermediate Similarity	NPC471104
0.7733	Intermediate Similarity	NPC472572
0.7733	Intermediate Similarity	NPC469349
0.7733	Intermediate Similarity	NPC301946
0.7733	Intermediate Similarity	NPC472556
0.7733	Intermediate Similarity	NPC96903
0.7733	Intermediate Similarity	NPC472568
0.7733	Intermediate Similarity	NPC472575
0.7733	Intermediate Similarity	NPC476973
0.7733	Intermediate Similarity	NPC471100
0.7733	Intermediate Similarity	NPC177940
0.7733	Intermediate Similarity	NPC471107
0.7719	Intermediate Similarity	NPC477894
0.7697	Intermediate Similarity	NPC469417
0.7688	Intermediate Similarity	NPC94602
0.7684	Intermediate Similarity	NPC251139
0.768	Intermediate Similarity	NPC66193
0.7674	Intermediate Similarity	NPC25768
0.7674	Intermediate Similarity	NPC470152
0.7674	Intermediate Similarity	NPC475122
0.7674	Intermediate Similarity	NPC241951
0.7674	Intermediate Similarity	NPC11685
0.7674	Intermediate Similarity	NPC472573
0.7674	Intermediate Similarity	NPC475759
0.7674	Intermediate Similarity	NPC70716
0.7674	Intermediate Similarity	NPC188865
0.7674	Intermediate Similarity	NPC125106
0.7674	Intermediate Similarity	NPC95810
0.7674	Intermediate Similarity	NPC476974
0.7674	Intermediate Similarity	NPC80895
0.7674	Intermediate Similarity	NPC472570
0.7674	Intermediate Similarity	NPC472569
0.7674	Intermediate Similarity	NPC163719
0.7674	Intermediate Similarity	NPC471912
0.7674	Intermediate Similarity	NPC95265
0.7674	Intermediate Similarity	NPC57628
0.763	Intermediate Similarity	NPC473541
0.7624	Intermediate Similarity	NPC253738
0.7616	Intermediate Similarity	NPC163087
0.7609	Intermediate Similarity	NPC102465
0.7602	Intermediate Similarity	NPC213567
0.7602	Intermediate Similarity	NPC97947
0.7602	Intermediate Similarity	NPC118080
0.7602	Intermediate Similarity	NPC87448
0.7602	Intermediate Similarity	NPC16912
0.7602	Intermediate Similarity	NPC41481
0.7602	Intermediate Similarity	NPC224491
0.7602	Intermediate Similarity	NPC472576
0.7602	Intermediate Similarity	NPC27377
0.7602	Intermediate Similarity	NPC291599
0.76	Intermediate Similarity	NPC301556
0.76	Intermediate Similarity	NPC270590
0.76	Intermediate Similarity	NPC92293
0.76	Intermediate Similarity	NPC266265
0.76	Intermediate Similarity	NPC471101
0.7596	Intermediate Similarity	NPC61891
0.7596	Intermediate Similarity	NPC30171
0.7574	Intermediate Similarity	NPC472374
0.7574	Intermediate Similarity	NPC472372
0.7572	Intermediate Similarity	NPC260194
0.7572	Intermediate Similarity	NPC470231
0.7571	Intermediate Similarity	NPC469648
0.7571	Intermediate Similarity	NPC138641
0.7571	Intermediate Similarity	NPC283875
0.7571	Intermediate Similarity	NPC469647
0.7571	Intermediate Similarity	NPC22571
0.7558	Intermediate Similarity	NPC472546
0.7544	Intermediate Similarity	NPC275592
0.7544	Intermediate Similarity	NPC472547
0.7544	Intermediate Similarity	NPC100913
0.7544	Intermediate Similarity	NPC97667
0.7544	Intermediate Similarity	NPC171207
0.7544	Intermediate Similarity	NPC90614
0.7543	Intermediate Similarity	NPC281717
0.7543	Intermediate Similarity	NPC473760
0.7528	Intermediate Similarity	NPC133430
0.7528	Intermediate Similarity	NPC469477
0.7527	Intermediate Similarity	NPC55744
0.7515	Intermediate Similarity	NPC477893
0.7515	Intermediate Similarity	NPC477896
0.7514	Intermediate Similarity	NPC472398
0.7514	Intermediate Similarity	NPC40138
0.7512	Intermediate Similarity	NPC96801
0.7512	Intermediate Similarity	NPC150698
0.7486	Intermediate Similarity	NPC209592
0.7486	Intermediate Similarity	NPC5115
0.7486	Intermediate Similarity	NPC150893

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 NPC475336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	536
0.2-0.3	1018
0.3-0.4	2295
0.4-0.5	3270
0.5-0.6	1570
0.6-0.7	255
0.7-0.8	17
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9713	High Similarity	NPD8485	Approved
0.9708	High Similarity	NPD8360	Approved
0.9708	High Similarity	NPD8361	Approved
0.9593	High Similarity	NPD8435	Approved
0.9548	High Similarity	NPD8486	Clinical (unspecified phase)
0.9253	High Similarity	NPD8424	Clinical (unspecified phase)
0.8966	High Similarity	NPD8368	Discontinued
0.892	High Similarity	NPD8407	Phase 2
0.8686	High Similarity	NPD8470	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD8462	Phase 1
0.8325	Intermediate Similarity	NPD8404	Phase 2
0.7725	Intermediate Similarity	NPD8150	Discontinued
0.7632	Intermediate Similarity	NPD8434	Phase 2
0.7488	Intermediate Similarity	NPD7874	Approved
0.7488	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7801	Approved
0.7413	Intermediate Similarity	NPD8320	Phase 1
0.7413	Intermediate Similarity	NPD8319	Approved
0.7374	Intermediate Similarity	NPD7700	Phase 2
0.7374	Intermediate Similarity	NPD7699	Phase 2
0.731	Intermediate Similarity	NPD6534	Approved
0.731	Intermediate Similarity	NPD6535	Approved
0.7299	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5030	Phase 2
0.7273	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7799	Discontinued
0.724	Intermediate Similarity	NPD5028	Approved
0.724	Intermediate Similarity	NPD5034	Approved
0.724	Intermediate Similarity	NPD5026	Approved
0.724	Intermediate Similarity	NPD36	Approved
0.724	Intermediate Similarity	NPD4954	Approved
0.724	Intermediate Similarity	NPD4955	Approved
0.7216	Intermediate Similarity	NPD5036	Approved
0.7184	Intermediate Similarity	NPD8151	Discontinued
0.7179	Intermediate Similarity	NPD5038	Approved
0.7179	Intermediate Similarity	NPD5037	Approved
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7136	Intermediate Similarity	NPD7701	Phase 2
0.7135	Intermediate Similarity	NPD7236	Approved
0.7129	Intermediate Similarity	NPD6778	Approved
0.7129	Intermediate Similarity	NPD6780	Approved
0.7129	Intermediate Similarity	NPD6776	Approved
0.7129	Intermediate Similarity	NPD6782	Approved
0.7129	Intermediate Similarity	NPD6781	Approved
0.7129	Intermediate Similarity	NPD6777	Approved
0.7129	Intermediate Similarity	NPD6779	Approved
0.7127	Intermediate Similarity	NPD7239	Suspended
0.7108	Intermediate Similarity	NPD7696	Phase 3
0.7108	Intermediate Similarity	NPD7697	Approved
0.7108	Intermediate Similarity	NPD7698	Approved
0.7073	Intermediate Similarity	NPD7871	Phase 2
0.7073	Intermediate Similarity	NPD7870	Phase 2
0.7047	Intermediate Similarity	NPD3823	Discontinued
0.7035	Intermediate Similarity	NPD8468	Phase 2
0.7024	Intermediate Similarity	NPD7435	Discontinued
0.6961	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5035	Approved
0.6923	Remote Similarity	NPD5031	Approved
0.6923	Remote Similarity	NPD5027	Approved
0.6923	Remote Similarity	NPD5029	Approved
0.6897	Remote Similarity	NPD7282	Approved
0.6875	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5968	Phase 3
0.6866	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7497	Discontinued
0.6854	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6836	Approved
0.6818	Remote Similarity	NPD8059	Phase 3
0.6818	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7783	Phase 2
0.6792	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7972	Discontinued
0.6743	Remote Similarity	NPD7907	Approved
0.672	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4914	Approved
0.67	Remote Similarity	NPD3819	Phase 2
0.6684	Remote Similarity	NPD7058	Phase 2
0.6684	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD7565	Approved
0.6667	Remote Similarity	NPD7810	Phase 3
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7811	Phase 3
0.6667	Remote Similarity	NPD6213	Phase 3
0.6652	Remote Similarity	NPD8067	Phase 3
0.6651	Remote Similarity	NPD4665	Approved
0.6648	Remote Similarity	NPD2575	Approved
0.6633	Remote Similarity	NPD5032	Approved
0.6612	Remote Similarity	NPD6190	Approved
0.6604	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8366	Approved
0.6587	Remote Similarity	NPD8285	Discontinued
0.6587	Remote Similarity	NPD5544	Approved
0.658	Remote Similarity	NPD6746	Phase 2
0.6576	Remote Similarity	NPD3300	Phase 2
0.6575	Remote Similarity	NPD4111	Phase 1
0.6571	Remote Similarity	NPD4387	Approved
0.6571	Remote Similarity	NPD4386	Approved
0.6564	Remote Similarity	NPD5242	Approved
0.6562	Remote Similarity	NPD7075	Discontinued
0.6547	Remote Similarity	NPD8491	Approved
0.6536	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.652	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7473	Discontinued
0.6492	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7460	Discontinued
0.6474	Remote Similarity	NPD6386	Approved
0.6474	Remote Similarity	NPD6385	Approved
0.6468	Remote Similarity	NPD7930	Approved
0.6467	Remote Similarity	NPD3400	Discontinued
0.6467	Remote Similarity	NPD4628	Phase 3
0.6461	Remote Similarity	NPD7713	Phase 3
0.6461	Remote Similarity	NPD7715	Approved
0.6461	Remote Similarity	NPD7714	Approved
0.6458	Remote Similarity	NPD5402	Approved
0.6457	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD8146	Phase 2
0.6449	Remote Similarity	NPD7583	Approved
0.6449	Remote Similarity	NPD7584	Approved
0.6447	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD2494	Approved
0.6445	Remote Similarity	NPD2493	Approved
0.6445	Remote Similarity	NPD3450	Approved
0.6445	Remote Similarity	NPD3452	Approved
0.6441	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7029	Discontinued
0.644	Remote Similarity	NPD6801	Discontinued
0.6436	Remote Similarity	NPD8312	Approved
0.6436	Remote Similarity	NPD8313	Approved
0.6432	Remote Similarity	NPD5844	Phase 1
0.6432	Remote Similarity	NPD4583	Approved
0.6432	Remote Similarity	NPD4582	Approved
0.6429	Remote Similarity	NPD7315	Approved
0.6425	Remote Similarity	NPD4466	Phase 1
0.6421	Remote Similarity	NPD6599	Discontinued
0.6421	Remote Similarity	NPD4380	Phase 2
0.6419	Remote Similarity	NPD7585	Approved
0.6411	Remote Similarity	NPD2973	Approved
0.6411	Remote Similarity	NPD2975	Approved
0.6411	Remote Similarity	NPD2974	Approved
0.6408	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7819	Suspended
0.6402	Remote Similarity	NPD7999	Approved
0.64	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4580	Approved
0.6386	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7962	Phase 2
0.6385	Remote Similarity	NPD4002	Approved
0.6385	Remote Similarity	NPD4004	Approved
0.6384	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7177	Discontinued
0.6382	Remote Similarity	NPD3751	Discontinued
0.6381	Remote Similarity	NPD4975	Approved
0.6381	Remote Similarity	NPD4974	Approved
0.6378	Remote Similarity	NPD8166	Discontinued
0.6368	Remote Similarity	NPD3455	Phase 2
0.6368	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6166	Phase 2
0.6364	Remote Similarity	NPD7048	Phase 3
0.6358	Remote Similarity	NPD6287	Discontinued
0.6354	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6874	Approved
0.6351	Remote Similarity	NPD5609	Approved
0.6351	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5608	Approved
0.635	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4738	Phase 2
0.6345	Remote Similarity	NPD6232	Discontinued
0.6341	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD3057	Approved
0.6337	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7038	Approved
0.6337	Remote Similarity	NPD5039	Approved
0.6337	Remote Similarity	NPD7039	Approved
0.6333	Remote Similarity	NPD5120	Approved
0.6333	Remote Similarity	NPD5121	Approved
0.6333	Remote Similarity	NPD5119	Approved
0.6311	Remote Similarity	NPD7693	Approved
0.6305	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8367	Approved
0.6302	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7827	Phase 1
0.6296	Remote Similarity	NPD6296	Discontinued
0.6294	Remote Similarity	NPD8127	Discontinued
0.6292	Remote Similarity	NPD4620	Approved
0.6292	Remote Similarity	NPD5201	Approved
0.6292	Remote Similarity	NPD4617	Approved
0.6292	Remote Similarity	NPD5203	Approved
0.6289	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3817	Phase 2
0.6287	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5157	Phase 1
0.6286	Remote Similarity	NPD5159	Phase 2

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