NPASS Compound

Structure

NPC290683 OpenBabel07101718232D 46 53 0 0 1 0 0 0 0 0999 V2000 -1.3254 -2.0533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4002 -2.2025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1114 -3.2905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7193 -0.4346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7525 -3.5826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6339 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2539 -2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7591 -1.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1613 -2.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6942 -2.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2953 -2.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0273 -2.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6046 -0.7260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0659 -2.7531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2953 -1.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0273 -1.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2011 -0.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5807 -0.7002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4292 0.2310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4195 -1.6298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5068 -2.4940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7206 -0.4855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7315 -2.5828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1613 -0.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9104 -2.0121 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7617 0.6932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1994 -1.0548 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5280 -1.9782 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7078 -0.0783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6533 1.1459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1613 0.2310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8061 -0.2391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3334 -0.6335 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5632 0.7310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6284 0.0150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1992 -1.0338 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5596 -0.2862 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4854 -2.2672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0273 0.7310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7855 -0.4411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5501 -0.0974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2953 0.7310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4676 1.7264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0128 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3347 -0.5869 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 33 1 0 0 0 0 19 34 1 0 0 0 0 19 42 1 0 0 0 0 20 33 1 0 0 0 0 21 3 1 1 0 0 0 21 25 1 0 0 0 0 22 37 1 1 0 0 0 23 5 1 6 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 44 1 0 0 0 0 30 34 1 0 0 0 0 30 43 1 0 0 0 0 31 39 2 0 0 0 0 31 42 1 0 0 0 0 32 34 1 0 0 0 0 32 36 1 0 0 0 0 32 40 1 0 0 0 0 33 45 1 0 0 0 0 34 43 1 0 0 0 0 35 44 1 0 0 0 0 35 45 1 0 0 0 0 35 46 1 0 0 0 0 36 41 1 0 0 0 0 37 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.35
Volume:	645.986
LogP:	5.893
LogD:	4.541
LogS:	-4.007
# Rotatable Bonds:	5
TPSA:	127.21
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.248
Synthetic Accessibility Score:	7.837
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:	-4.976
MDCK Permeability:	3.679972360259853e-05
Pgp-inhibitor:	0.947
Pgp-substrate:	0.826
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.56
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	98.7337417602539%
Volume Distribution (VD):	2.311
Pgp-substrate:	1.6584539413452148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.677
CYP2C9-inhibitor:	0.754
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	10.015
Half-life (T1/2):	0.462

ADMET: Toxicity

hERG Blockers:	0.834
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.448
Rat Oral Acute Toxicity:	0.436
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.445
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC290683

Natural Product ID:	NPC290683
*Common Name:**	LVCUWWNEJYSTOS-RVXSWFTCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LVCUWWNEJYSTOS-RVXSWFTCSA-N
Standard InCHI:	InChI=1S/C37H50O9/c1-20(2)33-18-22(4)37-26-29(33)44-35(45-33,46-37)17-13-8-6-7-10-14-21(3)25-23(5)28(38)36(41,27(25)37)32(40)34(30(26)43-34)19-42-31(39)24-15-11-9-12-16-24/h9,11-12,15-16,21-23,25-30,32,38,40-41H,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:	C[C@@H]1CCCCCCC[C@@]23O[C@]45[C@@H]6[C@@H]1[C@H](C)[C@@H]([C@@]6(O)[C@H](O)[C@@]1([C@H]([C@H]5[C@@H](O2)[C@](C[C@H]4C)(O3)C(=C)C)O1)COC(=O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2376809
PubChem CID:	73350390
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	=	18690.0	nM	PMID[564902]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	16490.0	nM	PMID[564902]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	18080.0	nM	PMID[564902]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	9560.0	nM	PMID[564902]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	18780.0	nM	PMID[564902]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	28920.0	nM	PMID[564902]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	11350.0	nM	PMID[564902]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	19910.0	nM	PMID[564902]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[564902]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29360.0	nM	PMID[564902]

☑ 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 NPC290683 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	350
0.1-0.2	1212
0.2-0.3	2629
0.3-0.4	5501
0.4-0.5	10379
0.5-0.6	15286
0.6-0.7	6102
0.7-0.8	955
0.8-0.85	191
0.85-0.9	55
0.9-0.95	22
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475548
1.0	High Similarity	NPC475638
0.9862	High Similarity	NPC471135
0.9797	High Similarity	NPC323356
0.9797	High Similarity	NPC326328
0.9797	High Similarity	NPC471138
0.9797	High Similarity	NPC309991
0.9662	High Similarity	NPC322048
0.9662	High Similarity	NPC318447
0.9595	High Similarity	NPC326235
0.9595	High Similarity	NPC323001
0.9536	High Similarity	NPC478124
0.9346	High Similarity	NPC478125
0.9338	High Similarity	NPC319404
0.9324	High Similarity	NPC62792
0.9315	High Similarity	NPC312393
0.931	High Similarity	NPC471139
0.9257	High Similarity	NPC476173
0.9231	High Similarity	NPC40138
0.9195	High Similarity	NPC298072
0.9195	High Similarity	NPC478123
0.9156	High Similarity	NPC43304
0.9156	High Similarity	NPC477188
0.9156	High Similarity	NPC477190
0.9122	High Similarity	NPC327031
0.9103	High Similarity	NPC325078
0.9103	High Similarity	NPC324769
0.9103	High Similarity	NPC325732
0.8981	High Similarity	NPC61891
0.8961	High Similarity	NPC49297
0.8954	High Similarity	NPC154675
0.8933	High Similarity	NPC76103
0.8926	High Similarity	NPC240115
0.8896	High Similarity	NPC181924
0.8861	High Similarity	NPC477491
0.8854	High Similarity	NPC66193
0.8854	High Similarity	NPC322420
0.8824	High Similarity	NPC472657
0.8824	High Similarity	NPC472658
0.8816	High Similarity	NPC96308
0.88	High Similarity	NPC478263
0.8797	High Similarity	NPC471134
0.8792	High Similarity	NPC34943
0.879	High Similarity	NPC275477
0.8733	High Similarity	NPC478264
0.8725	High Similarity	NPC131966
0.8725	High Similarity	NPC191387
0.8718	High Similarity	NPC476784
0.8716	High Similarity	NPC97947
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
0.8716	High Similarity	NPC291599
0.8701	High Similarity	NPC146310
0.8696	High Similarity	NPC477488
0.8693	High Similarity	NPC469415
0.8675	High Similarity	NPC20255
0.8658	High Similarity	NPC192658
0.8649	High Similarity	NPC275592
0.8649	High Similarity	NPC97667
0.8649	High Similarity	NPC171207
0.8649	High Similarity	NPC90614
0.8649	High Similarity	NPC100913
0.8645	High Similarity	NPC34066
0.8645	High Similarity	NPC251139
0.8645	High Similarity	NPC469422
0.8627	High Similarity	NPC303429
0.8627	High Similarity	NPC222102
0.8625	High Similarity	NPC473468
0.8625	High Similarity	NPC473557
0.8625	High Similarity	NPC475567
0.8618	High Similarity	NPC473760
0.8609	High Similarity	NPC184817
0.8609	High Similarity	NPC469349
0.8609	High Similarity	NPC70403
0.8609	High Similarity	NPC470159
0.8609	High Similarity	NPC158663
0.8609	High Similarity	NPC125882
0.8609	High Similarity	NPC96903
0.8609	High Similarity	NPC177940
0.8609	High Similarity	NPC311825
0.8609	High Similarity	NPC171525
0.8609	High Similarity	NPC472571
0.8609	High Similarity	NPC200471
0.8609	High Similarity	NPC476973
0.8609	High Similarity	NPC92867
0.8609	High Similarity	NPC472568
0.8609	High Similarity	NPC472575
0.8609	High Similarity	NPC473088
0.8609	High Similarity	NPC471104
0.8609	High Similarity	NPC470157
0.8609	High Similarity	NPC29704
0.8609	High Similarity	NPC174982
0.8609	High Similarity	NPC472572
0.8571	High Similarity	NPC475175
0.8571	High Similarity	NPC475531
0.8571	High Similarity	NPC475198
0.8553	High Similarity	NPC473602
0.8553	High Similarity	NPC48599
0.8553	High Similarity	NPC209592
0.8544	High Similarity	NPC477623
0.8543	High Similarity	NPC475759
0.8543	High Similarity	NPC188865
0.8543	High Similarity	NPC25768
0.8543	High Similarity	NPC476974
0.8543	High Similarity	NPC472570
0.8543	High Similarity	NPC95265
0.8543	High Similarity	NPC241951
0.8543	High Similarity	NPC472573
0.8543	High Similarity	NPC475122
0.8543	High Similarity	NPC11685
0.8543	High Similarity	NPC95810
0.8543	High Similarity	NPC57628
0.8543	High Similarity	NPC472569
0.8543	High Similarity	NPC70716
0.8543	High Similarity	NPC163719
0.8543	High Similarity	NPC125106
0.8543	High Similarity	NPC470152
0.8533	High Similarity	NPC34012
0.8526	High Similarity	NPC469398
0.8526	High Similarity	NPC469456
0.8526	High Similarity	NPC471176
0.8523	High Similarity	NPC162613
0.8523	High Similarity	NPC472547
0.8523	High Similarity	NPC87934
0.8506	High Similarity	NPC475561
0.8506	High Similarity	NPC469448
0.8506	High Similarity	NPC475417
0.8477	Intermediate Similarity	NPC163087
0.8471	Intermediate Similarity	NPC70344
0.8467	Intermediate Similarity	NPC266374
0.8462	Intermediate Similarity	NPC133430
0.8462	Intermediate Similarity	NPC469477
0.8462	Intermediate Similarity	NPC186746
0.8456	Intermediate Similarity	NPC9905
0.8442	Intermediate Similarity	NPC270590
0.8442	Intermediate Similarity	NPC266265
0.8442	Intermediate Similarity	NPC471101
0.8442	Intermediate Similarity	NPC92293
0.8442	Intermediate Similarity	NPC476975
0.8442	Intermediate Similarity	NPC301556
0.8431	Intermediate Similarity	NPC474935
0.8397	Intermediate Similarity	NPC138641
0.8397	Intermediate Similarity	NPC469647
0.8397	Intermediate Similarity	NPC22571
0.8397	Intermediate Similarity	NPC469648
0.8397	Intermediate Similarity	NPC145649
0.8397	Intermediate Similarity	NPC283875
0.8397	Intermediate Similarity	NPC233581
0.8389	Intermediate Similarity	NPC39549
0.8387	Intermediate Similarity	NPC473214
0.8387	Intermediate Similarity	NPC470245
0.8387	Intermediate Similarity	NPC31829
0.8378	Intermediate Similarity	NPC291638
0.8378	Intermediate Similarity	NPC17877
0.8378	Intermediate Similarity	NPC66761
0.8378	Intermediate Similarity	NPC200154
0.8378	Intermediate Similarity	NPC472577
0.8378	Intermediate Similarity	NPC195647
0.8377	Intermediate Similarity	NPC281717
0.8366	Intermediate Similarity	NPC472556
0.8365	Intermediate Similarity	NPC469399
0.8355	Intermediate Similarity	NPC477894
0.8355	Intermediate Similarity	NPC91703
0.8354	Intermediate Similarity	NPC11410
0.8333	Intermediate Similarity	NPC121268
0.8333	Intermediate Similarity	NPC53361
0.8333	Intermediate Similarity	NPC470153
0.8333	Intermediate Similarity	NPC473301
0.8323	Intermediate Similarity	NPC473215
0.8323	Intermediate Similarity	NPC55744
0.8322	Intermediate Similarity	NPC472545
0.8322	Intermediate Similarity	NPC472551
0.8312	Intermediate Similarity	NPC477737
0.8311	Intermediate Similarity	NPC474608
0.8301	Intermediate Similarity	NPC38696
0.8291	Intermediate Similarity	NPC132599
0.8291	Intermediate Similarity	NPC469730
0.8291	Intermediate Similarity	NPC473632
0.8291	Intermediate Similarity	NPC473611
0.8289	Intermediate Similarity	NPC472546
0.828	Intermediate Similarity	NPC472548
0.828	Intermediate Similarity	NPC477905
0.8278	Intermediate Similarity	NPC48017
0.8278	Intermediate Similarity	NPC473060
0.8278	Intermediate Similarity	NPC473085
0.8278	Intermediate Similarity	NPC4341
0.8278	Intermediate Similarity	NPC476094
0.8278	Intermediate Similarity	NPC200592
0.8278	Intermediate Similarity	NPC147880
0.8278	Intermediate Similarity	NPC43241
0.8278	Intermediate Similarity	NPC473758
0.8278	Intermediate Similarity	NPC473112
0.8278	Intermediate Similarity	NPC473081
0.8278	Intermediate Similarity	NPC211137
0.8278	Intermediate Similarity	NPC473613
0.8278	Intermediate Similarity	NPC184747

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 NPC290683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	788
0.2-0.3	1676
0.3-0.4	3135
0.4-0.5	2203
0.5-0.6	864
0.6-0.7	190
0.7-0.8	11
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
0.8193	Intermediate Similarity	NPD7799	Discontinued
0.7785	Intermediate Similarity	NPD7236	Approved
0.7719	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7685	Pre-registration
0.7654	Intermediate Similarity	NPD7239	Suspended
0.76	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8407	Phase 2
0.7486	Intermediate Similarity	NPD8368	Discontinued
0.7451	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5126	Approved
0.7248	Intermediate Similarity	NPD5125	Phase 3
0.7235	Intermediate Similarity	NPD7058	Phase 2
0.7235	Intermediate Similarity	NPD7057	Phase 3
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD4966	Approved
0.7135	Intermediate Similarity	NPD4965	Approved
0.7135	Intermediate Similarity	NPD4967	Phase 2
0.7104	Intermediate Similarity	NPD8435	Approved
0.7104	Intermediate Similarity	NPD8360	Approved
0.7104	Intermediate Similarity	NPD8361	Approved
0.7088	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8127	Discontinued
0.7069	Intermediate Similarity	NPD7199	Phase 2
0.7062	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD37	Approved
0.7052	Intermediate Similarity	NPD6234	Discontinued
0.7027	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7497	Discontinued
0.7	Intermediate Similarity	NPD7741	Discontinued
0.6974	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD8312	Approved
0.6919	Remote Similarity	NPD5760	Phase 2
0.6919	Remote Similarity	NPD5761	Phase 2
0.6906	Remote Similarity	NPD6764	Approved
0.6906	Remote Similarity	NPD6559	Discontinued
0.6906	Remote Similarity	NPD6765	Approved
0.6906	Remote Similarity	NPD7240	Approved
0.6905	Remote Similarity	NPD6273	Approved
0.6902	Remote Similarity	NPD8150	Discontinued
0.6893	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7028	Phase 2
0.6833	Remote Similarity	NPD5844	Phase 1
0.6829	Remote Similarity	NPD5763	Approved
0.6829	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6005	Phase 3
0.6829	Remote Similarity	NPD5762	Approved
0.6829	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6004	Phase 3
0.6829	Remote Similarity	NPD7266	Discontinued
0.6829	Remote Similarity	NPD6002	Phase 3
0.6821	Remote Similarity	NPD8455	Phase 2
0.6821	Remote Similarity	NPD7819	Suspended
0.6813	Remote Similarity	NPD7961	Discontinued
0.6807	Remote Similarity	NPD4628	Phase 3
0.6803	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7999	Approved
0.6766	Remote Similarity	NPD6190	Approved
0.6757	Remote Similarity	NPD6785	Approved
0.6757	Remote Similarity	NPD6784	Approved
0.675	Remote Similarity	NPD3764	Approved
0.6738	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD8462	Phase 1
0.6733	Remote Similarity	NPD2629	Approved
0.6724	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7516	Approved
0.6708	Remote Similarity	NPD6663	Approved
0.6705	Remote Similarity	NPD7075	Discontinued
0.6705	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8485	Approved
0.6686	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD7930	Approved
0.6667	Remote Similarity	NPD7700	Phase 2
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7507	Approved
0.6648	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4380	Phase 2
0.6646	Remote Similarity	NPD7319	Approved
0.6645	Remote Similarity	NPD7328	Approved
0.6645	Remote Similarity	NPD7327	Approved
0.6644	Remote Similarity	NPD6685	Approved
0.6633	Remote Similarity	NPD8319	Approved
0.6633	Remote Similarity	NPD8320	Phase 1
0.6612	Remote Similarity	NPD7074	Phase 3
0.6607	Remote Similarity	NPD8166	Discontinued
0.6597	Remote Similarity	NPD6534	Approved
0.6597	Remote Similarity	NPD6535	Approved
0.6593	Remote Similarity	NPD3751	Discontinued
0.659	Remote Similarity	NPD7458	Discontinued
0.6584	Remote Similarity	NPD7008	Discontinued
0.6582	Remote Similarity	NPD7435	Discontinued
0.6579	Remote Similarity	NPD4198	Discontinued
0.6562	Remote Similarity	NPD5736	Approved
0.6557	Remote Similarity	NPD7054	Approved
0.6556	Remote Similarity	NPD3787	Discontinued
0.6554	Remote Similarity	NPD2182	Approved
0.6538	Remote Similarity	NPD7473	Discontinued
0.6536	Remote Similarity	NPD5494	Approved
0.6524	Remote Similarity	NPD6355	Discontinued
0.6522	Remote Similarity	NPD7472	Approved
0.6516	Remote Similarity	NPD8296	Approved
0.6516	Remote Similarity	NPD8380	Approved
0.6516	Remote Similarity	NPD8335	Approved
0.6516	Remote Similarity	NPD7503	Approved
0.6516	Remote Similarity	NPD8033	Approved
0.6516	Remote Similarity	NPD8379	Approved
0.6516	Remote Similarity	NPD8378	Approved
0.6512	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7808	Phase 3
0.65	Remote Similarity	NPD6085	Phase 2
0.65	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5402	Approved
0.6494	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6858	Approved
0.649	Remote Similarity	NPD7094	Approved
0.6486	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6653	Approved
0.648	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6801	Discontinued
0.6468	Remote Similarity	NPD7874	Approved
0.6468	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6232	Discontinued
0.6453	Remote Similarity	NPD2534	Approved
0.6453	Remote Similarity	NPD2533	Approved
0.6453	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD2532	Approved
0.6452	Remote Similarity	NPD7251	Discontinued
0.6452	Remote Similarity	NPD8377	Approved
0.6452	Remote Similarity	NPD8294	Approved
0.6447	Remote Similarity	NPD6823	Phase 2
0.6446	Remote Similarity	NPD7097	Phase 1
0.6441	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8404	Phase 2
0.6438	Remote Similarity	NPD5765	Approved
0.6429	Remote Similarity	NPD6780	Approved
0.6429	Remote Similarity	NPD6779	Approved
0.6429	Remote Similarity	NPD6778	Approved
0.6429	Remote Similarity	NPD2346	Discontinued
0.6429	Remote Similarity	NPD6781	Approved
0.6429	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6782	Approved
0.6429	Remote Similarity	NPD6777	Approved
0.6429	Remote Similarity	NPD6776	Approved
0.6424	Remote Similarity	NPD5735	Approved
0.6424	Remote Similarity	NPD969	Suspended
0.6424	Remote Similarity	NPD230	Phase 1
0.6424	Remote Similarity	NPD6912	Phase 3
0.6414	Remote Similarity	NPD7698	Approved
0.6414	Remote Similarity	NPD7697	Approved
0.6414	Remote Similarity	NPD7680	Approved
0.6414	Remote Similarity	NPD7696	Phase 3
0.6412	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2575	Approved
0.6405	Remote Similarity	NPD5951	Approved
0.6405	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3817	Phase 2
0.6398	Remote Similarity	NPD6797	Phase 2
0.6392	Remote Similarity	NPD7492	Approved
0.6387	Remote Similarity	NPD7610	Discontinued
0.6384	Remote Similarity	NPD1934	Approved
0.6382	Remote Similarity	NPD7870	Phase 2
0.6382	Remote Similarity	NPD7871	Phase 2
0.6379	Remote Similarity	NPD5403	Approved
0.6378	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7736	Approved
0.6369	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2935	Discontinued
0.6369	Remote Similarity	NPD7768	Phase 2
0.6369	Remote Similarity	NPD7137	Phase 2
0.6368	Remote Similarity	NPD7701	Phase 2
0.6364	Remote Similarity	NPD6599	Discontinued
0.6364	Remote Similarity	NPD4140	Approved
0.6358	Remote Similarity	NPD5401	Approved
0.6355	Remote Similarity	NPD7801	Approved
0.6353	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6674	Discontinued
0.6352	Remote Similarity	NPD6616	Approved
0.6346	Remote Similarity	NPD6054	Approved
0.6343	Remote Similarity	NPD1653	Approved
0.6337	Remote Similarity	NPD8151	Discontinued
0.6335	Remote Similarity	NPD3094	Phase 2
0.6333	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7411	Suspended
0.6327	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3750	Approved
0.6312	Remote Similarity	NPD7078	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