NPASS Compound

Structure

NPC471135 OpenBabel07101719402D 47 53 0 0 1 0 0 0 0 0999 V2000 -0.5534 2.6036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2024 2.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1806 -2.7033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2333 -1.4958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8831 -2.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8585 -2.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3288 -2.7342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1889 -1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3486 0.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2953 -2.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4825 0.0721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3486 1.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2546 -1.2360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8901 -2.6061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6165 0.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4825 2.0721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0426 -0.6443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9601 -0.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0184 2.0721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2250 1.8627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3379 -2.1650 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1885 -0.4969 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5177 -1.8248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6165 1.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5499 -1.5733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4750 0.9138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4901 -0.5750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0561 -0.9821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1552 1.6468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2761 1.0978 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7505 2.0721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7157 0.7459 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1524 1.5721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9191 0.9106 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5948 -0.2032 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.4210 -0.2097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6241 -0.0750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0543 -0.9223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7899 2.5777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7505 3.0721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7046 0.8949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1524 2.5721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 0.7903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8845 1.5721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8110 0.5393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0785 0.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 4 22 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 13 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 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 21 1 0 0 0 0 15 24 2 0 0 0 0 16 24 1 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 34 1 0 0 0 0 19 33 1 0 0 0 0 19 44 1 0 0 0 0 20 34 1 0 0 0 0 21 3 1 6 0 0 0 21 25 1 0 0 0 0 22 37 1 6 0 0 0 23 5 1 1 0 0 0 23 25 1 0 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 25 27 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 26 37 1 0 0 0 0 27 36 1 0 0 0 0 27 37 1 0 0 0 0 28 36 1 0 0 0 0 28 38 1 0 0 0 0 29 33 1 0 0 0 0 29 39 1 0 0 0 0 30 34 1 0 0 0 0 30 45 1 0 0 0 0 31 40 2 0 0 0 0 31 44 1 0 0 0 0 32 33 1 0 0 0 0 32 36 1 0 0 0 0 32 41 1 0 0 0 0 33 42 1 0 0 0 0 34 46 1 0 0 0 0 35 45 1 0 0 0 0 35 46 1 0 0 0 0 35 47 1 0 0 0 0 36 43 1 0 0 0 0 37 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.36
Volume:	663.333
LogP:	5.179
LogD:	4.15
LogS:	-3.709
# Rotatable Bonds:	5
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	7.822
Fsp3:	0.757
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:	-4.952
MDCK Permeability:	3.971522892243229e-05
Pgp-inhibitor:	0.532
Pgp-substrate:	0.958
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.746
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	98.17369079589844%
Volume Distribution (VD):	1.801
Pgp-substrate:	1.021087646484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.679
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.641
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	9.419
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.637
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.363
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC471135

Natural Product ID:	NPC471135
*Common Name:**	KUKFFCSAEKBDJN-OOOKLGDUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KUKFFCSAEKBDJN-OOOKLGDUSA-N
Standard InCHI:	InChI=1S/C37H52O10/c1-20(2)34-18-22(4)37-26-29(39)33(42,19-44-31(40)24-15-11-9-12-16-24)32(41)36(43)27(37)25(23(5)28(36)38)21(3)14-10-7-6-8-13-17-35(46-34,47-37)45-30(26)34/h9,11-12,15-16,21-23,25-30,32,38-39,41-43H,1,6-8,10,13-14,17-19H2,2-5H3/t21-,22-,23+,25+,26+,27-,28+,29+,30-,32-,33-,34-,35?,36-,37-/m1/s1
SMILES:	CC1CCCCCCCC23OC4C5C(C(C(C6(C(C1C(C6O)C)C5(O2)C(CC4(O3)C(=C)C)C)O)O)(COC(=O)C7=CC=CC=C7)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2376810
PubChem CID:	71601112
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	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	10

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[529324]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	50000.0	nM	PMID[529324]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[529324]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	7710.0	nM	PMID[529324]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	44990.0	nM	PMID[529324]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	50000.0	nM	PMID[529324]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	28550.0	nM	PMID[529324]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[529324]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	25150.0	nM	PMID[529324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28640.0	nM	PMID[529324]

☑ 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 NPC471135 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	335
0.1-0.2	1142
0.2-0.3	2531
0.3-0.4	5129
0.4-0.5	9907
0.5-0.6	14816
0.6-0.7	7428
0.7-0.8	1083
0.8-0.85	170
0.85-0.9	116
0.9-0.95	27
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC475548
0.9862	High Similarity	NPC475638
0.9862	High Similarity	NPC290683
0.9795	High Similarity	NPC318447
0.9795	High Similarity	NPC322048
0.9726	High Similarity	NPC326235
0.9726	High Similarity	NPC323001
0.9662	High Similarity	NPC471138
0.9662	High Similarity	NPC326328
0.9662	High Similarity	NPC323356
0.9662	High Similarity	NPC309991
0.9463	High Similarity	NPC319404
0.9444	High Similarity	NPC312393
0.9441	High Similarity	NPC471139
0.9404	High Similarity	NPC478124
0.9384	High Similarity	NPC476173
0.9247	High Similarity	NPC327031
0.9231	High Similarity	NPC325078
0.9216	High Similarity	NPC478125
0.9189	High Similarity	NPC62792
0.9103	High Similarity	NPC40138
0.906	High Similarity	NPC478123
0.906	High Similarity	NPC298072
0.9054	High Similarity	NPC76103
0.9048	High Similarity	NPC240115
0.9026	High Similarity	NPC477190
0.9026	High Similarity	NPC477188
0.9026	High Similarity	NPC43304
0.8974	High Similarity	NPC324769
0.8974	High Similarity	NPC325732
0.8968	High Similarity	NPC66193
0.8933	High Similarity	NPC96308
0.8919	High Similarity	NPC478263
0.8912	High Similarity	NPC34943
0.891	High Similarity	NPC471134
0.8854	High Similarity	NPC61891
0.8851	High Similarity	NPC478264
0.8836	High Similarity	NPC118080
0.8836	High Similarity	NPC472576
0.8836	High Similarity	NPC87448
0.8836	High Similarity	NPC291599
0.8836	High Similarity	NPC27377
0.8836	High Similarity	NPC41481
0.8836	High Similarity	NPC97947
0.8836	High Similarity	NPC16912
0.8831	High Similarity	NPC49297
0.8831	High Similarity	NPC476784
0.8824	High Similarity	NPC154675
0.8816	High Similarity	NPC472658
0.8816	High Similarity	NPC472657
0.8808	High Similarity	NPC469415
0.8792	High Similarity	NPC20255
0.8776	High Similarity	NPC192658
0.8767	High Similarity	NPC171207
0.8767	High Similarity	NPC97667
0.8767	High Similarity	NPC90614
0.8767	High Similarity	NPC275592
0.8767	High Similarity	NPC100913
0.8766	High Similarity	NPC181924
0.8758	High Similarity	NPC34066
0.8758	High Similarity	NPC469422
0.8742	High Similarity	NPC303429
0.8742	High Similarity	NPC222102
0.8734	High Similarity	NPC477491
0.8734	High Similarity	NPC473468
0.8734	High Similarity	NPC473557
0.8734	High Similarity	NPC475567
0.8733	High Similarity	NPC473760
0.8726	High Similarity	NPC322420
0.8725	High Similarity	NPC311825
0.8725	High Similarity	NPC29704
0.8725	High Similarity	NPC472571
0.8725	High Similarity	NPC177940
0.8725	High Similarity	NPC472572
0.8725	High Similarity	NPC200471
0.8725	High Similarity	NPC476973
0.8725	High Similarity	NPC92867
0.8725	High Similarity	NPC174982
0.8725	High Similarity	NPC472568
0.8725	High Similarity	NPC125882
0.8725	High Similarity	NPC96903
0.8725	High Similarity	NPC470157
0.8725	High Similarity	NPC473088
0.8725	High Similarity	NPC472575
0.8725	High Similarity	NPC469349
0.8725	High Similarity	NPC471104
0.8725	High Similarity	NPC158663
0.8725	High Similarity	NPC470159
0.8725	High Similarity	NPC70403
0.8725	High Similarity	NPC184817
0.8725	High Similarity	NPC171525
0.8716	High Similarity	NPC131966
0.8716	High Similarity	NPC191387
0.8679	High Similarity	NPC475175
0.8679	High Similarity	NPC475531
0.8679	High Similarity	NPC475198
0.8667	High Similarity	NPC48599
0.8667	High Similarity	NPC209592
0.8667	High Similarity	NPC473602
0.8662	High Similarity	NPC275477
0.8658	High Similarity	NPC125106
0.8658	High Similarity	NPC57628
0.8658	High Similarity	NPC472569
0.8658	High Similarity	NPC476974
0.8658	High Similarity	NPC472570
0.8658	High Similarity	NPC188865
0.8658	High Similarity	NPC25768
0.8658	High Similarity	NPC241951
0.8658	High Similarity	NPC472573
0.8658	High Similarity	NPC163719
0.8658	High Similarity	NPC475122
0.8658	High Similarity	NPC95265
0.8658	High Similarity	NPC475759
0.8658	High Similarity	NPC470152
0.8658	High Similarity	NPC11685
0.8658	High Similarity	NPC95810
0.8658	High Similarity	NPC70716
0.8654	High Similarity	NPC477623
0.8649	High Similarity	NPC34012
0.8639	High Similarity	NPC87934
0.8639	High Similarity	NPC472547
0.8639	High Similarity	NPC162613
0.8636	High Similarity	NPC469456
0.8636	High Similarity	NPC469398
0.8618	High Similarity	NPC469448
0.8591	High Similarity	NPC163087
0.8581	High Similarity	NPC70344
0.8581	High Similarity	NPC266374
0.8571	High Similarity	NPC469477
0.8571	High Similarity	NPC146310
0.8571	High Similarity	NPC477488
0.8571	High Similarity	NPC9905
0.8571	High Similarity	NPC133430
0.8553	High Similarity	NPC476975
0.8553	High Similarity	NPC471101
0.8553	High Similarity	NPC266265
0.8553	High Similarity	NPC92293
0.8553	High Similarity	NPC270590
0.8553	High Similarity	NPC301556
0.8543	High Similarity	NPC474935
0.8516	High Similarity	NPC251139
0.8503	High Similarity	NPC39549
0.8497	Intermediate Similarity	NPC470245
0.8497	Intermediate Similarity	NPC475417
0.8497	Intermediate Similarity	NPC475561
0.8497	Intermediate Similarity	NPC31829
0.8497	Intermediate Similarity	NPC473214
0.8493	Intermediate Similarity	NPC66761
0.8493	Intermediate Similarity	NPC17877
0.8493	Intermediate Similarity	NPC472577
0.8493	Intermediate Similarity	NPC291638
0.8493	Intermediate Similarity	NPC195647
0.8493	Intermediate Similarity	NPC200154
0.8487	Intermediate Similarity	NPC281717
0.8477	Intermediate Similarity	NPC472556
0.8471	Intermediate Similarity	NPC469399
0.8467	Intermediate Similarity	NPC91703
0.8446	Intermediate Similarity	NPC53361
0.8446	Intermediate Similarity	NPC473301
0.8446	Intermediate Similarity	NPC121268
0.8442	Intermediate Similarity	NPC470153
0.8435	Intermediate Similarity	NPC472545
0.8435	Intermediate Similarity	NPC472551
0.8431	Intermediate Similarity	NPC473215
0.8428	Intermediate Similarity	NPC55744
0.8425	Intermediate Similarity	NPC474608
0.8421	Intermediate Similarity	NPC477737
0.8411	Intermediate Similarity	NPC38696
0.84	Intermediate Similarity	NPC472546
0.8397	Intermediate Similarity	NPC473632
0.8397	Intermediate Similarity	NPC473611
0.8397	Intermediate Similarity	NPC132599
0.8397	Intermediate Similarity	NPC469730
0.8397	Intermediate Similarity	NPC471176
0.8389	Intermediate Similarity	NPC473112
0.8389	Intermediate Similarity	NPC473081
0.8389	Intermediate Similarity	NPC211137
0.8389	Intermediate Similarity	NPC476094
0.8389	Intermediate Similarity	NPC184747
0.8389	Intermediate Similarity	NPC48017
0.8389	Intermediate Similarity	NPC4341
0.8389	Intermediate Similarity	NPC473613
0.8389	Intermediate Similarity	NPC147880
0.8389	Intermediate Similarity	NPC473109
0.8389	Intermediate Similarity	NPC473085
0.8389	Intermediate Similarity	NPC473060
0.8389	Intermediate Similarity	NPC200592
0.8389	Intermediate Similarity	NPC43241
0.8389	Intermediate Similarity	NPC473758
0.8387	Intermediate Similarity	NPC283875
0.8387	Intermediate Similarity	NPC472548
0.8387	Intermediate Similarity	NPC233581
0.8387	Intermediate Similarity	NPC138641
0.8387	Intermediate Similarity	NPC469647
0.8387	Intermediate Similarity	NPC145649
0.8387	Intermediate Similarity	NPC22571
0.8387	Intermediate Similarity	NPC477905
0.8387	Intermediate Similarity	NPC469648
0.8378	Intermediate Similarity	NPC327511
0.8378	Intermediate Similarity	NPC205305

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 NPC471135 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	751
0.2-0.3	1613
0.3-0.4	3051
0.4-0.5	2283
0.5-0.6	949
0.6-0.7	217
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD7799	Discontinued
0.7885	Intermediate Similarity	NPD7236	Approved
0.7811	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7239	Suspended
0.7703	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8407	Phase 2
0.7572	Intermediate Similarity	NPD8368	Discontinued
0.7572	Intermediate Similarity	NPD7685	Pre-registration
0.755	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5125	Phase 3
0.7347	Intermediate Similarity	NPD5126	Approved
0.7321	Intermediate Similarity	NPD7058	Phase 2
0.7321	Intermediate Similarity	NPD7057	Phase 3
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD4966	Approved
0.7219	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD4965	Approved
0.7182	Intermediate Similarity	NPD8361	Approved
0.7182	Intermediate Similarity	NPD8435	Approved
0.7182	Intermediate Similarity	NPD8360	Approved
0.7151	Intermediate Similarity	NPD7199	Phase 2
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD6234	Discontinued
0.7104	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7741	Discontinued
0.709	Intermediate Similarity	NPD7497	Discontinued
0.7072	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD5760	Phase 2
0.6988	Remote Similarity	NPD6273	Approved
0.6983	Remote Similarity	NPD6765	Approved
0.6983	Remote Similarity	NPD7240	Approved
0.6983	Remote Similarity	NPD6559	Discontinued
0.6983	Remote Similarity	NPD6764	Approved
0.6978	Remote Similarity	NPD8150	Discontinued
0.6971	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7028	Phase 2
0.6914	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6005	Phase 3
0.6914	Remote Similarity	NPD5762	Approved
0.6914	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7266	Discontinued
0.6914	Remote Similarity	NPD6004	Phase 3
0.6914	Remote Similarity	NPD6002	Phase 3
0.6914	Remote Similarity	NPD5763	Approved
0.691	Remote Similarity	NPD5844	Phase 1
0.6901	Remote Similarity	NPD7819	Suspended
0.6901	Remote Similarity	NPD8455	Phase 2
0.6899	Remote Similarity	NPD7961	Discontinued
0.6897	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4628	Phase 3
0.6864	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6190	Approved
0.6835	Remote Similarity	NPD3764	Approved
0.6831	Remote Similarity	NPD6784	Approved
0.6831	Remote Similarity	NPD6785	Approved
0.6824	Remote Similarity	NPD2629	Approved
0.6811	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8462	Phase 1
0.68	Remote Similarity	NPD7516	Approved
0.6792	Remote Similarity	NPD6663	Approved
0.6782	Remote Similarity	NPD7075	Discontinued
0.6782	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8485	Approved
0.6766	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.676	Remote Similarity	NPD3818	Discontinued
0.6753	Remote Similarity	NPD7507	Approved
0.6747	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7699	Phase 2
0.6737	Remote Similarity	NPD7700	Phase 2
0.6736	Remote Similarity	NPD6685	Approved
0.6733	Remote Similarity	NPD7328	Approved
0.6733	Remote Similarity	NPD7327	Approved
0.6731	Remote Similarity	NPD7319	Approved
0.6725	Remote Similarity	NPD4380	Phase 2
0.6724	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8319	Approved
0.6701	Remote Similarity	NPD8320	Phase 1
0.6687	Remote Similarity	NPD8166	Discontinued
0.6685	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD7999	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD6534	Approved
0.6649	Remote Similarity	NPD7435	Discontinued
0.6646	Remote Similarity	NPD5736	Approved
0.6644	Remote Similarity	NPD2182	Approved
0.663	Remote Similarity	NPD7054	Approved
0.6611	Remote Similarity	NPD7473	Discontinued
0.661	Remote Similarity	NPD5494	Approved
0.6605	Remote Similarity	NPD6355	Discontinued
0.6601	Remote Similarity	NPD8033	Approved
0.6601	Remote Similarity	NPD8378	Approved
0.6601	Remote Similarity	NPD8296	Approved
0.6601	Remote Similarity	NPD8380	Approved
0.6601	Remote Similarity	NPD8335	Approved
0.6601	Remote Similarity	NPD7503	Approved
0.6601	Remote Similarity	NPD8379	Approved
0.6593	Remote Similarity	NPD7472	Approved
0.6587	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6085	Phase 2
0.6577	Remote Similarity	NPD6858	Approved
0.6577	Remote Similarity	NPD7094	Approved
0.6576	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7808	Phase 3
0.6571	Remote Similarity	NPD5402	Approved
0.657	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7930	Approved
0.6564	Remote Similarity	NPD6653	Approved
0.6557	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6801	Discontinued
0.6536	Remote Similarity	NPD6232	Discontinued
0.6536	Remote Similarity	NPD8377	Approved
0.6536	Remote Similarity	NPD8294	Approved
0.6533	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7874	Approved
0.6529	Remote Similarity	NPD2532	Approved
0.6529	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2534	Approved
0.6529	Remote Similarity	NPD2533	Approved
0.6528	Remote Similarity	NPD5765	Approved
0.6524	Remote Similarity	NPD7097	Phase 1
0.6522	Remote Similarity	NPD7251	Discontinued
0.6514	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6823	Phase 2
0.651	Remote Similarity	NPD969	Suspended
0.651	Remote Similarity	NPD6912	Phase 3
0.6506	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2346	Discontinued
0.6503	Remote Similarity	NPD230	Phase 1
0.6503	Remote Similarity	NPD5735	Approved
0.6502	Remote Similarity	NPD8404	Phase 2
0.6495	Remote Similarity	NPD6780	Approved
0.6495	Remote Similarity	NPD6776	Approved
0.6495	Remote Similarity	NPD6777	Approved
0.6495	Remote Similarity	NPD6779	Approved
0.6495	Remote Similarity	NPD6782	Approved
0.6495	Remote Similarity	NPD6781	Approved
0.6495	Remote Similarity	NPD6778	Approved
0.649	Remote Similarity	NPD690	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5951	Approved
0.6488	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3751	Discontinued
0.648	Remote Similarity	NPD7680	Approved
0.648	Remote Similarity	NPD7697	Approved
0.648	Remote Similarity	NPD7696	Phase 3
0.648	Remote Similarity	NPD7698	Approved
0.6477	Remote Similarity	NPD3817	Phase 2
0.6477	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD7610	Discontinued
0.6467	Remote Similarity	NPD6797	Phase 2
0.6457	Remote Similarity	NPD1934	Approved
0.6456	Remote Similarity	NPD7736	Approved
0.6453	Remote Similarity	NPD5403	Approved
0.6452	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7871	Phase 2
0.6447	Remote Similarity	NPD7870	Phase 2
0.6446	Remote Similarity	NPD7137	Phase 2
0.6446	Remote Similarity	NPD2935	Discontinued
0.6444	Remote Similarity	NPD3787	Discontinued
0.6443	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4140	Approved
0.6441	Remote Similarity	NPD7768	Phase 2
0.6437	Remote Similarity	NPD6599	Discontinued
0.6433	Remote Similarity	NPD6616	Approved
0.6433	Remote Similarity	NPD5401	Approved
0.6432	Remote Similarity	NPD7701	Phase 2
0.6429	Remote Similarity	NPD6054	Approved
0.6429	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6674	Discontinued
0.6419	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7801	Approved
0.6416	Remote Similarity	NPD1653	Approved
0.6415	Remote Similarity	NPD3094	Phase 2
0.6414	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7411	Suspended
0.64	Remote Similarity	NPD8151	Discontinued
0.6395	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7078	Approved
0.6391	Remote Similarity	NPD3750	Approved
0.6386	Remote Similarity	NPD2799	Discontinued

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