NPASS Compound

Structure

CID146310 OpenBabel06191715502D 35 41 0 0 1 0 0 0 0 0999 V2000 -3.2764 -1.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2532 -2.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6561 4.2376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7638 1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0472 -1.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3730 -2.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0472 -1.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6988 -1.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3730 -0.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4370 2.4121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8931 -0.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4776 1.9644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5113 -1.2663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1192 3.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3515 0.5444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6988 -1.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5610 1.7537 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4962 -0.1871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0751 3.6186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3183 -1.3694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6617 0.0792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6612 2.2336 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8796 -0.8113 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1802 1.1565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4955 2.4993 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5613 0.5581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0135 -0.7784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3260 2.1107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5492 4.3371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1978 2.9068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2435 2.0732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8539 0.1689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5280 -1.3556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9445 -0.1378 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 13 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 14 19 1 0 0 0 0 15 26 1 1 0 0 0 17 25 1 1 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 18 26 1 6 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 23 1 1 0 0 0 20 33 1 0 0 0 0 21 24 1 6 0 0 0 21 32 1 0 0 0 0 22 24 1 1 0 0 0 22 25 1 0 0 0 0 22 30 1 0 0 0 0 23 13 1 1 0 0 0 23 34 1 0 0 0 0 24 12 1 1 0 0 0 24 32 1 0 0 0 0 25 31 1 1 0 0 0 26 35 1 1 0 0 0 27 16 1 1 0 0 0 27 33 1 0 0 0 0 27 34 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.19
Volume:	470.156
LogP:	2.655
LogD:	2.09
LogS:	-4.056
# Rotatable Bonds:	3
TPSA:	117.98
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	6.42
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.187
MDCK Permeability:	2.8154496249044314e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.095
30% Bioavailability (F30%):	0.716

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.752
Plasma Protein Binding (PPB):	68.44881439208984%
Volume Distribution (VD):	2.154
Pgp-substrate:	29.526594161987305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.573

ADMET: Excretion

Clearance (CL):	3.057
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.86
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.64
Carcinogencity:	0.85
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC146310

Natural Product ID:	NPC146310
*Common Name:**	Daphnetoxin
IUPAC Name:	n.a.
Synonyms:	Daphnetoxin
Standard InCHIKey:	LGEROVMQYFTBDI-FFIGBMOQSA-N
Standard InCHI:	InChI=1S/C27H30O8/c1-13(2)23-11-15(4)26-17-10-14(3)19(29)25(17,31)22(30)24(12-28)21(32-24)18(26)20(23)33-27(34-23,35-26)16-8-6-5-7-9-16/h5-10,15,17-18,20-22,28,30-31H,1,11-12H2,2-4H3/t15-,17-,18-,20-,21+,22-,23-,24+,25-,26+,27-/m1/s1
SMILES:	OC[C@]12O[C@H]1[C@H]1[C@H]3O[C@]4(O[C@]1([C@H]1[C@@]([C@@H]2O)(O)C(=O)C(=C1)C)[C@@H](C[C@@]3(O4)C(=C)C)C)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023369
PubChem CID:	119454
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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	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
EC50	4
Others	2

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	16.2	nM	PMID[454235]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	26.7	nM	PMID[454235]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	21.0	nM	PMID[454235]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Ratio EC50	=	1.0	n.a.	PMID[454235]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	22.0	nM	PMID[454235]

☑ 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 NPC146310 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	366
0.1-0.2	1172
0.2-0.3	2617
0.3-0.4	5194
0.4-0.5	10125
0.5-0.6	12594
0.6-0.7	9330
0.7-0.8	1041
0.8-0.85	208
0.85-0.9	16
0.9-0.95	17
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC181924
0.9728	High Similarity	NPC49297
0.9533	High Similarity	NPC43304
0.9533	High Similarity	NPC477188
0.9533	High Similarity	NPC477190
0.9533	High Similarity	NPC275477
0.9346	High Similarity	NPC61891
0.9329	High Similarity	NPC154675
0.9216	High Similarity	NPC66193
0.9216	High Similarity	NPC322420
0.9103	High Similarity	NPC40138
0.9007	High Similarity	NPC251139
0.8974	High Similarity	NPC324769
0.8974	High Similarity	NPC325732
0.891	High Similarity	NPC471134
0.8792	High Similarity	NPC477737
0.8701	High Similarity	NPC290683
0.8701	High Similarity	NPC475638
0.8701	High Similarity	NPC475548
0.8581	High Similarity	NPC11410
0.8571	High Similarity	NPC471135
0.8571	High Similarity	NPC469477
0.8571	High Similarity	NPC133430
0.8562	High Similarity	NPC471103
0.8554	High Similarity	NPC254588
0.8535	High Similarity	NPC309991
0.8535	High Similarity	NPC471138
0.8535	High Similarity	NPC323356
0.8535	High Similarity	NPC326328
0.8442	Intermediate Similarity	NPC51602
0.8442	Intermediate Similarity	NPC62792
0.8411	Intermediate Similarity	NPC471139
0.8408	Intermediate Similarity	NPC318447
0.8408	Intermediate Similarity	NPC322048
0.8387	Intermediate Similarity	NPC283875
0.8387	Intermediate Similarity	NPC138641
0.8387	Intermediate Similarity	NPC469647
0.8387	Intermediate Similarity	NPC22571
0.8387	Intermediate Similarity	NPC469648
0.8377	Intermediate Similarity	NPC476173
0.8355	Intermediate Similarity	NPC127857
0.8354	Intermediate Similarity	NPC469399
0.8344	Intermediate Similarity	NPC106895
0.8344	Intermediate Similarity	NPC323001
0.8344	Intermediate Similarity	NPC326235
0.8343	Intermediate Similarity	NPC186746
0.8333	Intermediate Similarity	NPC77493
0.8323	Intermediate Similarity	NPC298072
0.8323	Intermediate Similarity	NPC478123
0.8313	Intermediate Similarity	NPC478124
0.8312	Intermediate Similarity	NPC250046
0.8312	Intermediate Similarity	NPC81698
0.8312	Intermediate Similarity	NPC60509
0.8291	Intermediate Similarity	NPC469417
0.8291	Intermediate Similarity	NPC477735
0.828	Intermediate Similarity	NPC473670
0.828	Intermediate Similarity	NPC21410
0.828	Intermediate Similarity	NPC472549
0.828	Intermediate Similarity	NPC282239
0.828	Intermediate Similarity	NPC5115
0.8272	Intermediate Similarity	NPC477491
0.8269	Intermediate Similarity	NPC145649
0.8269	Intermediate Similarity	NPC233581
0.8261	Intermediate Similarity	NPC478073
0.8258	Intermediate Similarity	NPC161239
0.8258	Intermediate Similarity	NPC198455
0.8258	Intermediate Similarity	NPC7095
0.8258	Intermediate Similarity	NPC165260
0.8247	Intermediate Similarity	NPC132652
0.8239	Intermediate Similarity	NPC477736
0.8235	Intermediate Similarity	NPC301946
0.8235	Intermediate Similarity	NPC471100
0.8235	Intermediate Similarity	NPC277053
0.8235	Intermediate Similarity	NPC471107
0.8217	Intermediate Similarity	NPC248265
0.8217	Intermediate Similarity	NPC11588
0.8217	Intermediate Similarity	NPC229545
0.8217	Intermediate Similarity	NPC219419
0.8217	Intermediate Similarity	NPC134685
0.8212	Intermediate Similarity	NPC325078
0.821	Intermediate Similarity	NPC471493
0.8205	Intermediate Similarity	NPC472398
0.8199	Intermediate Similarity	NPC55744
0.8194	Intermediate Similarity	NPC475606
0.8194	Intermediate Similarity	NPC251564
0.8194	Intermediate Similarity	NPC475314
0.8194	Intermediate Similarity	NPC477189
0.8182	Intermediate Similarity	NPC469513
0.8176	Intermediate Similarity	NPC472393
0.8171	Intermediate Similarity	NPC102465
0.817	Intermediate Similarity	NPC80895
0.817	Intermediate Similarity	NPC471912
0.8165	Intermediate Similarity	NPC259144
0.8165	Intermediate Similarity	NPC114357
0.8165	Intermediate Similarity	NPC469730
0.8165	Intermediate Similarity	NPC155329
0.8165	Intermediate Similarity	NPC132599
0.8165	Intermediate Similarity	NPC26033
0.8165	Intermediate Similarity	NPC228204
0.8165	Intermediate Similarity	NPC473632
0.8153	Intermediate Similarity	NPC472548
0.8153	Intermediate Similarity	NPC477905
0.8148	Intermediate Similarity	NPC478125
0.8141	Intermediate Similarity	NPC112216
0.8141	Intermediate Similarity	NPC91730
0.8141	Intermediate Similarity	NPC222102
0.8141	Intermediate Similarity	NPC303429
0.8138	Intermediate Similarity	NPC473485
0.8138	Intermediate Similarity	NPC474508
0.8125	Intermediate Similarity	NPC471102
0.8125	Intermediate Similarity	NPC319404
0.8121	Intermediate Similarity	NPC477488
0.8113	Intermediate Similarity	NPC217091
0.8105	Intermediate Similarity	NPC477894
0.8101	Intermediate Similarity	NPC265395
0.8101	Intermediate Similarity	NPC473414
0.8101	Intermediate Similarity	NPC472005
0.8101	Intermediate Similarity	NPC472030
0.8101	Intermediate Similarity	NPC158333
0.8101	Intermediate Similarity	NPC242262
0.8101	Intermediate Similarity	NPC304876
0.8101	Intermediate Similarity	NPC257213
0.8101	Intermediate Similarity	NPC237549
0.8101	Intermediate Similarity	NPC256142
0.8101	Intermediate Similarity	NPC1173
0.8101	Intermediate Similarity	NPC249471
0.8101	Intermediate Similarity	NPC472022
0.8092	Intermediate Similarity	NPC118080
0.8092	Intermediate Similarity	NPC87448
0.8092	Intermediate Similarity	NPC27377
0.8092	Intermediate Similarity	NPC291599
0.8092	Intermediate Similarity	NPC97947
0.8092	Intermediate Similarity	NPC41481
0.8092	Intermediate Similarity	NPC472576
0.8089	Intermediate Similarity	NPC197037
0.8089	Intermediate Similarity	NPC101043
0.8089	Intermediate Similarity	NPC306799
0.8089	Intermediate Similarity	NPC469415
0.8089	Intermediate Similarity	NPC470153
0.8065	Intermediate Similarity	NPC312393
0.8065	Intermediate Similarity	NPC240115
0.805	Intermediate Similarity	NPC469456
0.805	Intermediate Similarity	NPC114410
0.805	Intermediate Similarity	NPC473611
0.805	Intermediate Similarity	NPC34066
0.805	Intermediate Similarity	NPC469422
0.805	Intermediate Similarity	NPC112523
0.8039	Intermediate Similarity	NPC182869
0.8039	Intermediate Similarity	NPC140021
0.8039	Intermediate Similarity	NPC183540
0.8037	Intermediate Similarity	NPC329960
0.8037	Intermediate Similarity	NPC295408
0.8037	Intermediate Similarity	NPC150893
0.8027	Intermediate Similarity	NPC471137
0.8027	Intermediate Similarity	NPC475154
0.8027	Intermediate Similarity	NPC223356
0.8027	Intermediate Similarity	NPC473548
0.8027	Intermediate Similarity	NPC471136
0.8027	Intermediate Similarity	NPC475500
0.8027	Intermediate Similarity	NPC100017
0.8027	Intermediate Similarity	NPC182266
0.8026	Intermediate Similarity	NPC275592
0.8026	Intermediate Similarity	NPC171207
0.8026	Intermediate Similarity	NPC100913
0.8026	Intermediate Similarity	NPC97667
0.8026	Intermediate Similarity	NPC90614
0.8025	Intermediate Similarity	NPC473214
0.8025	Intermediate Similarity	NPC470245
0.8025	Intermediate Similarity	NPC254558
0.8013	Intermediate Similarity	NPC217918
0.8012	Intermediate Similarity	NPC108191
0.8012	Intermediate Similarity	NPC93685
0.8012	Intermediate Similarity	NPC477471
0.8012	Intermediate Similarity	NPC477469
0.8012	Intermediate Similarity	NPC477466
0.8012	Intermediate Similarity	NPC477473
0.8	Intermediate Similarity	NPC70344
0.8	Intermediate Similarity	NPC162495
0.7988	Intermediate Similarity	NPC477627
0.7987	Intermediate Similarity	NPC95449
0.7987	Intermediate Similarity	NPC77719
0.7976	Intermediate Similarity	NPC469421
0.7975	Intermediate Similarity	NPC475536
0.7975	Intermediate Similarity	NPC165234
0.7974	Intermediate Similarity	NPC16912
0.7962	Intermediate Similarity	NPC476975
0.7962	Intermediate Similarity	NPC473215
0.7952	Intermediate Similarity	NPC469420
0.795	Intermediate Similarity	NPC469771
0.7937	Intermediate Similarity	NPC469398
0.7937	Intermediate Similarity	NPC471176
0.7935	Intermediate Similarity	NPC34943
0.7935	Intermediate Similarity	NPC475759
0.7935	Intermediate Similarity	NPC241951
0.7935	Intermediate Similarity	NPC470152
0.7927	Intermediate Similarity	NPC473641
0.7927	Intermediate Similarity	NPC475464
0.7927	Intermediate Similarity	NPC473797
0.7927	Intermediate Similarity	NPC475437
0.7927	Intermediate Similarity	NPC475300

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 NPC146310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	763
0.2-0.3	1664
0.3-0.4	3158
0.4-0.5	2184
0.5-0.6	859
0.6-0.7	211
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8012	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7799	Discontinued
0.7746	Intermediate Similarity	NPD8407	Phase 2
0.7674	Intermediate Similarity	NPD8368	Discontinued
0.7442	Intermediate Similarity	NPD3751	Discontinued
0.7438	Intermediate Similarity	NPD7236	Approved
0.7412	Intermediate Similarity	NPD3787	Discontinued
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7347	Intermediate Similarity	NPD5125	Phase 3
0.7347	Intermediate Similarity	NPD5126	Approved
0.7317	Intermediate Similarity	NPD7239	Suspended
0.7299	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8361	Approved
0.7278	Intermediate Similarity	NPD8360	Approved
0.7278	Intermediate Similarity	NPD8435	Approved
0.7198	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6190	Approved
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7118	Intermediate Similarity	NPD4965	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.7118	Intermediate Similarity	NPD4966	Approved
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7072	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3818	Discontinued
0.7041	Intermediate Similarity	NPD37	Approved
0.7035	Intermediate Similarity	NPD6234	Discontinued
0.7021	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7058	Phase 2
0.7018	Intermediate Similarity	NPD7057	Phase 3
0.7005	Intermediate Similarity	NPD7700	Phase 2
0.7005	Intermediate Similarity	NPD7699	Phase 2
0.6987	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7685	Pre-registration
0.6977	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7199	Phase 2
0.6949	Remote Similarity	NPD7228	Approved
0.6931	Remote Similarity	NPD6782	Approved
0.6931	Remote Similarity	NPD6780	Approved
0.6931	Remote Similarity	NPD6781	Approved
0.6931	Remote Similarity	NPD6777	Approved
0.6931	Remote Similarity	NPD6779	Approved
0.6931	Remote Similarity	NPD6776	Approved
0.6931	Remote Similarity	NPD6778	Approved
0.6928	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4380	Phase 2
0.691	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5494	Approved
0.6889	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD7075	Discontinued
0.6862	Remote Similarity	NPD8485	Approved
0.6851	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6797	Phase 2
0.6823	Remote Similarity	NPD7435	Discontinued
0.6802	Remote Similarity	NPD5761	Phase 2
0.6802	Remote Similarity	NPD8462	Phase 1
0.6802	Remote Similarity	NPD5760	Phase 2
0.6796	Remote Similarity	NPD7240	Approved
0.6796	Remote Similarity	NPD7251	Discontinued
0.6795	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8319	Approved
0.6788	Remote Similarity	NPD8320	Phase 1
0.6778	Remote Similarity	NPD7074	Phase 3
0.6758	Remote Similarity	NPD7808	Phase 3
0.6753	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6801	Discontinued
0.6742	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6166	Phase 2
0.6742	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7698	Approved
0.6736	Remote Similarity	NPD7697	Approved
0.6736	Remote Similarity	NPD7696	Phase 3
0.6725	Remote Similarity	NPD7028	Phase 2
0.6724	Remote Similarity	NPD3882	Suspended
0.6722	Remote Similarity	NPD7054	Approved
0.6721	Remote Similarity	NPD8313	Approved
0.6721	Remote Similarity	NPD8312	Approved
0.6711	Remote Similarity	NPD2629	Approved
0.6705	Remote Similarity	NPD7819	Suspended
0.6705	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6764	Approved
0.6703	Remote Similarity	NPD6765	Approved
0.6701	Remote Similarity	NPD7870	Phase 2
0.6701	Remote Similarity	NPD7871	Phase 2
0.6685	Remote Similarity	NPD7472	Approved
0.6684	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1934	Approved
0.6645	Remote Similarity	NPD7741	Discontinued
0.6645	Remote Similarity	NPD6054	Approved
0.6631	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5844	Phase 1
0.6628	Remote Similarity	NPD6599	Discontinued
0.6616	Remote Similarity	NPD7874	Approved
0.6616	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6213	Phase 3
0.6614	Remote Similarity	NPD6212	Phase 3
0.6611	Remote Similarity	NPD7473	Discontinued
0.6606	Remote Similarity	NPD7266	Discontinued
0.6601	Remote Similarity	NPD6015	Approved
0.6601	Remote Similarity	NPD6016	Approved
0.6587	Remote Similarity	NPD4628	Phase 3
0.6587	Remote Similarity	NPD2575	Approved
0.6584	Remote Similarity	NPD8404	Phase 2
0.6573	Remote Similarity	NPD8127	Discontinued
0.6568	Remote Similarity	NPD6799	Approved
0.6559	Remote Similarity	NPD6784	Approved
0.6559	Remote Similarity	NPD6785	Approved
0.6558	Remote Similarity	NPD5988	Approved
0.6558	Remote Similarity	NPD6370	Approved
0.6557	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6232	Discontinued
0.6534	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2532	Approved
0.6529	Remote Similarity	NPD2534	Approved
0.6529	Remote Similarity	NPD2533	Approved
0.6519	Remote Similarity	NPD7319	Approved
0.6514	Remote Similarity	NPD2801	Approved
0.6513	Remote Similarity	NPD6823	Phase 2
0.651	Remote Similarity	NPD969	Suspended
0.6506	Remote Similarity	NPD5762	Approved
0.6506	Remote Similarity	NPD5763	Approved
0.6497	Remote Similarity	NPD7999	Approved
0.649	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7930	Approved
0.6477	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7492	Approved
0.6474	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5403	Approved
0.6452	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3317	Approved
0.6443	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6616	Approved
0.6433	Remote Similarity	NPD5401	Approved
0.6429	Remote Similarity	NPD6059	Approved
0.642	Remote Similarity	NPD3764	Approved
0.642	Remote Similarity	NPD8455	Phase 2
0.641	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2346	Discontinued
0.6407	Remote Similarity	NPD6002	Phase 3
0.6407	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6004	Phase 3
0.6407	Remote Similarity	NPD6005	Phase 3
0.6402	Remote Similarity	NPD6355	Discontinued
0.64	Remote Similarity	NPD7411	Suspended
0.6396	Remote Similarity	NPD7497	Discontinued
0.6392	Remote Similarity	NPD7078	Approved
0.6391	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8166	Discontinued
0.6389	Remote Similarity	NPD6959	Discontinued
0.6386	Remote Similarity	NPD7033	Discontinued
0.638	Remote Similarity	NPD7961	Discontinued
0.6379	Remote Similarity	NPD7458	Discontinued
0.6379	Remote Similarity	NPD3226	Approved
0.6376	Remote Similarity	NPD2067	Discontinued
0.6375	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6085	Phase 2
0.6369	Remote Similarity	NPD2424	Discontinued
0.6369	Remote Similarity	NPD1549	Phase 2
0.6352	Remote Similarity	NPD7736	Approved
0.6351	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD2796	Approved
0.6347	Remote Similarity	NPD6100	Approved
0.6347	Remote Similarity	NPD6099	Approved
0.6337	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6674	Discontinued
0.6329	Remote Similarity	NPD7507	Approved
0.6327	Remote Similarity	NPD5048	Discontinued
0.6325	Remote Similarity	NPD7097	Phase 1
0.6323	Remote Similarity	NPD6319	Approved
0.6319	Remote Similarity	NPD3926	Phase 2
0.6318	Remote Similarity	NPD8151	Discontinued
0.6316	Remote Similarity	NPD6010	Discontinued
0.6316	Remote Similarity	NPD3300	Phase 2
0.6313	Remote Similarity	NPD3749	Approved
0.631	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1471	Phase 3
0.631	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD230	Phase 1
0.6302	Remote Similarity	NPD7296	Approved
0.6301	Remote Similarity	NPD1512	Approved
0.6301	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD1247	Approved
0.6294	Remote Similarity	NPD6398	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