NPASS Compound

Structure

CID317882 OpenBabel06191716142D 58 63 0 0 1 0 0 0 0 0999 V2000 -8.3425 -4.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0982 0.5550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 3.0974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4826 3.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5648 3.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2491 0.8552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4873 -4.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7529 -3.8787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3319 -5.2957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2166 3.0580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8976 -4.2329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1872 -4.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5975 -4.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8623 2.2028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6531 3.7924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3080 -4.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7184 -3.8144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9446 2.0820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7353 3.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1632 -3.6694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8017 -1.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0960 1.4008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9257 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4560 1.2217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0695 2.2033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5736 -3.4601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3810 2.8164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7329 0.9838 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6033 -0.9257 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9257 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2841 -2.7516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7208 1.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6944 -2.5423 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.9603 1.0413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9600 -1.9788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8017 0.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4975 0.2396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5621 1.3570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4633 2.6955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0808 -1.0610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9191 2.3983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6033 -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 -1.0249 2.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5497 -2.1881 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9637 1.9637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4050 -1.3885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1393 -2.3974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8781 0.9204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1048 -2.3331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0610 -0.4948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8997 3.4299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9361 -0.7068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6957 3.0238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9257 -0.9257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6120 0.0660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1090 1.8403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2396 0.8942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 41 1 0 0 0 0 5 41 1 0 0 0 0 7 8 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 26 2 0 0 0 0 17 26 1 0 0 0 0 18 27 2 0 0 0 0 19 27 1 0 0 0 0 20 31 1 0 0 0 0 21 29 1 0 0 0 0 21 30 1 0 0 0 0 22 28 1 0 0 0 0 22 44 1 0 0 0 0 23 43 1 0 0 0 0 23 55 1 0 0 0 0 24 28 1 0 0 0 0 24 32 2 0 0 0 0 25 46 2 0 0 0 0 25 58 1 0 0 0 0 26 33 1 0 0 0 0 27 39 1 0 0 0 0 28 56 1 6 0 0 0 29 42 1 6 0 0 0 29 47 1 0 0 0 0 30 43 1 6 0 0 0 30 55 1 0 0 0 0 31 45 2 3 0 0 0 31 48 1 0 0 0 0 32 34 1 0 0 0 0 32 41 1 0 0 0 0 33 35 1 0 0 0 0 33 45 1 0 0 0 0 34 37 1 0 0 0 0 34 49 1 6 0 0 0 35 40 1 0 0 0 0 35 50 1 6 0 0 0 36 38 1 0 0 0 0 36 42 1 6 0 0 0 36 43 1 0 0 0 0 37 42 1 0 0 0 0 37 51 2 0 0 0 0 38 44 1 1 0 0 0 38 57 1 0 0 0 0 39 52 2 0 0 0 0 39 57 1 0 0 0 0 40 53 2 0 0 0 0 40 56 1 0 0 0 0 41 44 1 0 0 0 0 42 6 1 6 0 0 0 43 58 1 1 0 0 0 44 54 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	805.37
Volume:	811.873
LogP:	3.97
LogD:	1.62
LogS:	-3.822
# Rotatable Bonds:	16
TPSA:	212.06
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	6.206
Fsp3:	0.591
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:	-5.372
MDCK Permeability:	4.829156387131661e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.122
20% Bioavailability (F20%):	0.844
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	95.31550598144531%
Volume Distribution (VD):	1.379
Pgp-substrate:	4.250408172607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.267
CYP2C9-inhibitor:	0.26
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.781

ADMET: Excretion

Clearance (CL):	4.722
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.644
Human Hepatotoxicity (H-HT):	0.941
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.092
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC317882

Natural Product ID:	NPC317882
*Common Name:**	OUZGCGZMZBOCBH-HGKICXJESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OUZGCGZMZBOCBH-HGKICXJESA-N
Standard InCHI:	InChI=1S/C44H55NO13/c1-7-8-11-20-31(48)45-33(26-16-12-9-13-17-26)35(50)40(53)56-28-22-44(54)38(57-39(52)27-18-14-10-15-19-27)36-42(6,37(51)34(49)32(24(28)2)41(44,4)5)29(47)21-30-43(36,23-55-30)58-25(3)46/h9-10,12-19,28-30,33-36,38,47,49-50,54H,7-8,11,20-23H2,1-6H3,(H,45,48)/t28-,29-,30+,33?,34+,35+,36-,38-,42+,43-,44+/m0/s1
SMILES:	CCCCCC(=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:	CHEMBL420691
PubChem CID:	5316384
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
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.24	ug.mL-1	PMID[552743]
NPT27	Others	Unspecified		IC50	=	0.0017	ug.mL-1	PMID[552743]

☑ 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 NPC317882 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	260
0.1-0.2	1019
0.2-0.3	2496
0.3-0.4	7059
0.4-0.5	13038
0.5-0.6	13802
0.6-0.7	4674
0.7-0.8	289
0.8-0.85	12
0.85-0.9	0
0.9-0.95	15
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471754
0.9882	High Similarity	NPC306001
0.9882	High Similarity	NPC473300
0.9882	High Similarity	NPC275170
0.9882	High Similarity	NPC324251
0.9882	High Similarity	NPC471629
0.9882	High Similarity	NPC473400
0.9882	High Similarity	NPC453583
0.9882	High Similarity	NPC475336
0.9882	High Similarity	NPC206211
0.9825	High Similarity	NPC33372
0.9825	High Similarity	NPC67246
0.9655	High Similarity	NPC321072
0.9655	High Similarity	NPC215892
0.9655	High Similarity	NPC242662
0.9655	High Similarity	NPC191193
0.96	High Similarity	NPC471606
0.96	High Similarity	NPC208553
0.96	High Similarity	NPC181964
0.9593	High Similarity	NPC471623
0.9548	High Similarity	NPC472375
0.9545	High Similarity	NPC473558
0.9438	High Similarity	NPC472392
0.9435	High Similarity	NPC473490
0.9385	High Similarity	NPC472391
0.931	High Similarity	NPC327699
0.9282	High Similarity	NPC289383
0.9231	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	NPC254558
0.7861	Intermediate Similarity	NPC473214
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	NPC471107
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
0.7719	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	NPC57628
0.7674	Intermediate Similarity	NPC95265
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	NPC270590
0.76	Intermediate Similarity	NPC301556
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
0.7568	Intermediate Similarity	NPC278272
0.7568	Intermediate Similarity	NPC120667
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
0.7513	Intermediate Similarity	NPC475649
0.7512	Intermediate Similarity	NPC96801
0.7512	Intermediate Similarity	NPC150698

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 NPC317882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	548
0.2-0.3	1023
0.3-0.4	2342
0.4-0.5	3275
0.5-0.6	1531
0.6-0.7	231
0.7-0.8	15
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9708	High Similarity	NPD8360	Approved
0.9708	High Similarity	NPD8361	Approved
0.96	High Similarity	NPD8485	Approved
0.9593	High Similarity	NPD8435	Approved
0.9438	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
0.7632	Intermediate Similarity	NPD8150	Discontinued
0.7632	Intermediate Similarity	NPD8434	Phase 2
0.7537	Intermediate Similarity	NPD7801	Approved
0.7488	Intermediate Similarity	NPD7874	Approved
0.7488	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
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)
0.7273	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7799	Discontinued
0.7188	Intermediate Similarity	NPD5030	Phase 2
0.715	Intermediate Similarity	NPD5034	Approved
0.715	Intermediate Similarity	NPD5026	Approved
0.715	Intermediate Similarity	NPD5028	Approved
0.715	Intermediate Similarity	NPD36	Approved
0.715	Intermediate Similarity	NPD4955	Approved
0.715	Intermediate Similarity	NPD4954	Approved
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
0.7128	Intermediate Similarity	NPD5036	Approved
0.7127	Intermediate Similarity	NPD7239	Suspended
0.7108	Intermediate Similarity	NPD7696	Phase 3
0.7108	Intermediate Similarity	NPD7698	Approved
0.7108	Intermediate Similarity	NPD7697	Approved
0.7101	Intermediate Similarity	NPD8151	Discontinued
0.7092	Intermediate Similarity	NPD5037	Approved
0.7092	Intermediate Similarity	NPD5038	Approved
0.7073	Intermediate Similarity	NPD7871	Phase 2
0.7073	Intermediate Similarity	NPD7870	Phase 2
0.7059	Intermediate Similarity	NPD6823	Phase 2
0.7035	Intermediate Similarity	NPD8468	Phase 2
0.7024	Intermediate Similarity	NPD7435	Discontinued
0.6961	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3823	Discontinued
0.6895	Remote Similarity	NPD8059	Phase 3
0.6895	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7497	Discontinued
0.6854	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5035	Approved
0.6845	Remote Similarity	NPD7972	Discontinued
0.6837	Remote Similarity	NPD5029	Approved
0.6837	Remote Similarity	NPD5031	Approved
0.6837	Remote Similarity	NPD5027	Approved
0.6814	Remote Similarity	NPD7282	Approved
0.6792	Remote Similarity	NPD7783	Phase 2
0.6792	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5968	Phase 3
0.6766	Remote Similarity	NPD6836	Approved
0.6743	Remote Similarity	NPD7907	Approved
0.672	Remote Similarity	NPD6591	Clinical (unspecified phase)
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
0.6651	Remote Similarity	NPD4665	Approved
0.6648	Remote Similarity	NPD2575	Approved
0.6635	Remote Similarity	NPD4914	Approved
0.6618	Remote Similarity	NPD3819	Phase 2
0.6615	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6190	Approved
0.6604	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8285	Discontinued
0.6579	Remote Similarity	NPD7460	Discontinued
0.6578	Remote Similarity	NPD8067	Phase 3
0.6575	Remote Similarity	NPD4111	Phase 1
0.6564	Remote Similarity	NPD5242	Approved
0.6562	Remote Similarity	NPD7075	Discontinued
0.655	Remote Similarity	NPD5032	Approved
0.6536	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7029	Discontinued
0.652	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD8366	Approved
0.6507	Remote Similarity	NPD5544	Approved
0.6497	Remote Similarity	NPD7473	Discontinued
0.6495	Remote Similarity	NPD6746	Phase 2
0.6493	Remote Similarity	NPD4387	Approved
0.6493	Remote Similarity	NPD4386	Approved
0.6492	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3300	Phase 2
0.6474	Remote Similarity	NPD6386	Approved
0.6474	Remote Similarity	NPD6385	Approved
0.6473	Remote Similarity	NPD8491	Approved
0.6468	Remote Similarity	NPD7930	Approved
0.6467	Remote Similarity	NPD4628	Phase 3
0.6467	Remote Similarity	NPD3400	Discontinued
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)
0.6449	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)
0.6441	Remote Similarity	NPD4738	Phase 2
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
0.6429	Remote Similarity	NPD6874	Approved
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
0.6378	Remote Similarity	NPD8166	Discontinued
0.6377	Remote Similarity	NPD8146	Phase 2
0.6376	Remote Similarity	NPD7827	Phase 1
0.6372	Remote Similarity	NPD6296	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
0.6354	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7011	Discontinued
0.6351	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4466	Phase 1
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
0.6308	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4975	Approved
0.6303	Remote Similarity	NPD4974	Approved
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	NPD5159	Phase 2
0.6286	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5157	Phase 1
0.6283	Remote Similarity	NPD7458	Discontinued
0.6281	Remote Similarity	NPD3451	Clinical (unspecified phase)

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