NPASS Compound

Structure

CID1408 OpenBabel06191715322D 36 40 0 0 1 0 0 0 0 0999 V2000 1.6923 -1.0713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0928 -4.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3426 1.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4575 1.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0163 -2.1359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2828 -3.0888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8692 1.4111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7585 -2.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5931 0.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7717 -2.6793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1606 -3.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5506 -3.8780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3940 1.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4123 -0.1807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7717 -1.6027 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0134 -4.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8060 0.7089 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7022 -2.3566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9473 0.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0928 -2.6793 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0950 -1.2095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2843 -0.4573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9130 -1.6244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7077 -0.5061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7323 0.7892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0928 -1.6027 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1606 -1.0645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9339 -4.8051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1525 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1024 -0.8722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5737 -3.4255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4423 0.7552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0134 -3.2107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8843 -1.9417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6790 -0.8234 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 31 1 0 0 0 0 13 32 1 0 0 0 0 14 21 1 0 0 0 0 15 27 1 6 0 0 0 16 28 2 0 0 0 0 16 33 1 0 0 0 0 17 14 1 1 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 18 31 1 0 0 0 0 19 24 1 0 0 0 0 19 32 1 0 0 0 0 20 26 1 6 0 0 0 20 33 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 27 1 6 0 0 0 22 35 1 0 0 0 0 23 29 2 0 0 0 0 23 34 1 0 0 0 0 24 30 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 27 1 6 0 0 0 27 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.2
Volume:	493.423
LogP:	4.286
LogD:	2.925
LogS:	-4.588
# Rotatable Bonds:	8
TPSA:	114.41
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	5.764
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
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:	-4.831
MDCK Permeability:	3.8313773984555155e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	85.13751983642578%
Volume Distribution (VD):	2.571
Pgp-substrate:	5.592181205749512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.713
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.576
CYP3A4-substrate:	0.364

ADMET: Excretion

Clearance (CL):	10.247
Half-life (T1/2):	0.443

ADMET: Toxicity

hERG Blockers:	0.934
Human Hepatotoxicity (H-HT):	0.786
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.09
Skin Sensitization:	0.062
Carcinogencity:	0.284
Eye Corrosion:	0.007
Eye Irritation:	0.363
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC1408

Natural Product ID:	NPC1408
*Common Name:**	Orbiculin D
IUPAC Name:	n.a.
Synonyms:	Orbiculin D
Standard InCHIKey:	YYBGZSCZDKPXGD-CLWMZTKQSA-N
Standard InCHI:	InChI=1S/C27H32O9/c1-15-10-11-20(33-16(2)28)26(5)21(34-23(29)18-8-6-12-31-18)14-17-22(27(15,26)36-25(17,3)4)35-24(30)19-9-7-13-32-19/h6-9,12-13,15,17,20-22H,10-11,14H2,1-5H3/t15-,17-,20+,21+,22-,26+,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@H]([C@@]2(C)[C@H](C[C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)c1ccco1)OC(=O)c1ccco1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493857
PubChem CID:	10649050
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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	5
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	36700.0	nM	PMID[456398]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	43600.0	nM	PMID[456398]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16800.0	nM	PMID[456399]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17800.0	nM	PMID[456399]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1200.0	nM	PMID[456399]
NPT2	Others	Unspecified		Ratio IC50	=	14.8	n.a.	PMID[456399]

☑ 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 NPC1408 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	403
0.1-0.2	1435
0.2-0.3	3053
0.3-0.4	6617
0.4-0.5	11883
0.5-0.6	7802
0.6-0.7	9914
0.7-0.8	1403
0.8-0.85	147
0.85-0.9	26
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246841
0.9673	High Similarity	NPC159520
0.9427	High Similarity	NPC88593
0.9355	High Similarity	NPC14499
0.9355	High Similarity	NPC475039
0.9355	High Similarity	NPC476035
0.8734	High Similarity	NPC195954
0.8696	High Similarity	NPC61967
0.8634	High Similarity	NPC285567
0.8625	High Similarity	NPC191828
0.8616	High Similarity	NPC88007
0.858	High Similarity	NPC126984
0.858	High Similarity	NPC27541
0.858	High Similarity	NPC276735
0.858	High Similarity	NPC62692
0.8571	High Similarity	NPC68848
0.8519	High Similarity	NPC283209
0.8516	High Similarity	NPC71821
0.85	High Similarity	NPC194499
0.8481	Intermediate Similarity	NPC308205
0.8481	Intermediate Similarity	NPC322546
0.8476	Intermediate Similarity	NPC473766
0.8476	Intermediate Similarity	NPC473753
0.8447	Intermediate Similarity	NPC473368
0.8438	Intermediate Similarity	NPC41880
0.8438	Intermediate Similarity	NPC104736
0.8415	Intermediate Similarity	NPC86800
0.8405	Intermediate Similarity	NPC471168
0.8397	Intermediate Similarity	NPC255414
0.8395	Intermediate Similarity	NPC8389
0.8385	Intermediate Similarity	NPC469847
0.8385	Intermediate Similarity	NPC304692
0.8373	Intermediate Similarity	NPC118086
0.8365	Intermediate Similarity	NPC182427
0.8365	Intermediate Similarity	NPC29695
0.8364	Intermediate Similarity	NPC270312
0.8354	Intermediate Similarity	NPC212257
0.8344	Intermediate Similarity	NPC188649
0.8344	Intermediate Similarity	NPC471003
0.8344	Intermediate Similarity	NPC79571
0.8323	Intermediate Similarity	NPC475237
0.8323	Intermediate Similarity	NPC294512
0.8323	Intermediate Similarity	NPC475641
0.8303	Intermediate Similarity	NPC121995
0.8303	Intermediate Similarity	NPC475779
0.8302	Intermediate Similarity	NPC18135
0.8302	Intermediate Similarity	NPC116717
0.8293	Intermediate Similarity	NPC288602
0.8293	Intermediate Similarity	NPC469846
0.8293	Intermediate Similarity	NPC88841
0.8291	Intermediate Similarity	NPC125182
0.8291	Intermediate Similarity	NPC69647
0.8274	Intermediate Similarity	NPC469848
0.8272	Intermediate Similarity	NPC214495
0.8272	Intermediate Similarity	NPC470119
0.8272	Intermediate Similarity	NPC7059
0.8263	Intermediate Similarity	NPC302392
0.8253	Intermediate Similarity	NPC476850
0.8253	Intermediate Similarity	NPC310572
0.8253	Intermediate Similarity	NPC476861
0.825	Intermediate Similarity	NPC294511
0.825	Intermediate Similarity	NPC121615
0.825	Intermediate Similarity	NPC268905
0.8242	Intermediate Similarity	NPC56358
0.8239	Intermediate Similarity	NPC228842
0.8232	Intermediate Similarity	NPC18986
0.8232	Intermediate Similarity	NPC471166
0.8232	Intermediate Similarity	NPC471167
0.8232	Intermediate Similarity	NPC470939
0.8221	Intermediate Similarity	NPC475295
0.8221	Intermediate Similarity	NPC473473
0.8204	Intermediate Similarity	NPC296558
0.8204	Intermediate Similarity	NPC291742
0.8193	Intermediate Similarity	NPC472141
0.8193	Intermediate Similarity	NPC277618
0.8187	Intermediate Similarity	NPC291150
0.8187	Intermediate Similarity	NPC240214
0.8176	Intermediate Similarity	NPC56953
0.8176	Intermediate Similarity	NPC176413
0.8176	Intermediate Similarity	NPC471001
0.8171	Intermediate Similarity	NPC305016
0.8171	Intermediate Similarity	NPC287559
0.816	Intermediate Similarity	NPC475066
0.816	Intermediate Similarity	NPC286722
0.816	Intermediate Similarity	NPC472283
0.816	Intermediate Similarity	NPC470118
0.816	Intermediate Similarity	NPC167142
0.8148	Intermediate Similarity	NPC476262
0.8148	Intermediate Similarity	NPC75310
0.8144	Intermediate Similarity	NPC472774
0.8144	Intermediate Similarity	NPC472775
0.8137	Intermediate Similarity	NPC476201
0.8133	Intermediate Similarity	NPC123088
0.8133	Intermediate Similarity	NPC476857
0.8133	Intermediate Similarity	NPC476858
0.8133	Intermediate Similarity	NPC476856
0.8129	Intermediate Similarity	NPC472665
0.8125	Intermediate Similarity	NPC5180
0.8121	Intermediate Similarity	NPC472668
0.8121	Intermediate Similarity	NPC82851
0.8113	Intermediate Similarity	NPC243165
0.8113	Intermediate Similarity	NPC19747
0.811	Intermediate Similarity	NPC472671
0.811	Intermediate Similarity	NPC475226
0.811	Intermediate Similarity	NPC237155
0.811	Intermediate Similarity	NPC475967
0.811	Intermediate Similarity	NPC84349
0.8107	Intermediate Similarity	NPC285227
0.8101	Intermediate Similarity	NPC62799
0.8098	Intermediate Similarity	NPC126723
0.8098	Intermediate Similarity	NPC209364
0.8098	Intermediate Similarity	NPC107646
0.8095	Intermediate Similarity	NPC271235
0.8089	Intermediate Similarity	NPC84479
0.8089	Intermediate Similarity	NPC251865
0.8086	Intermediate Similarity	NPC237259
0.8086	Intermediate Similarity	NPC98206
0.8086	Intermediate Similarity	NPC34421
0.8084	Intermediate Similarity	NPC308156
0.8081	Intermediate Similarity	NPC11062
0.8077	Intermediate Similarity	NPC121158
0.8072	Intermediate Similarity	NPC469338
0.8072	Intermediate Similarity	NPC472669
0.8072	Intermediate Similarity	NPC292389
0.807	Intermediate Similarity	NPC167340
0.8063	Intermediate Similarity	NPC211625
0.8061	Intermediate Similarity	NPC472653
0.8061	Intermediate Similarity	NPC25255
0.8061	Intermediate Similarity	NPC475381
0.805	Intermediate Similarity	NPC221809
0.8049	Intermediate Similarity	NPC197137
0.8038	Intermediate Similarity	NPC56731
0.8038	Intermediate Similarity	NPC34056
0.8038	Intermediate Similarity	NPC5676
0.8037	Intermediate Similarity	NPC471175
0.8036	Intermediate Similarity	NPC472651
0.8036	Intermediate Similarity	NPC173516
0.8036	Intermediate Similarity	NPC476853
0.8036	Intermediate Similarity	NPC476224
0.8025	Intermediate Similarity	NPC475777
0.8025	Intermediate Similarity	NPC472672
0.8025	Intermediate Similarity	NPC246164
0.8025	Intermediate Similarity	NPC205071
0.8024	Intermediate Similarity	NPC470940
0.8024	Intermediate Similarity	NPC261184
0.8024	Intermediate Similarity	NPC476860
0.8024	Intermediate Similarity	NPC469849
0.8024	Intermediate Similarity	NPC276551
0.8013	Intermediate Similarity	NPC20500
0.8012	Intermediate Similarity	NPC470792
0.8012	Intermediate Similarity	NPC472771
0.8012	Intermediate Similarity	NPC329938
0.8012	Intermediate Similarity	NPC156189
0.8012	Intermediate Similarity	NPC193798
0.8012	Intermediate Similarity	NPC6815
0.8012	Intermediate Similarity	NPC476122
0.8012	Intermediate Similarity	NPC294803
0.8	Intermediate Similarity	NPC105395
0.8	Intermediate Similarity	NPC247563
0.8	Intermediate Similarity	NPC242068
0.8	Intermediate Similarity	NPC477403
0.8	Intermediate Similarity	NPC474611
0.7988	Intermediate Similarity	NPC471397
0.7988	Intermediate Similarity	NPC60973
0.7988	Intermediate Similarity	NPC327922
0.7988	Intermediate Similarity	NPC263265
0.7988	Intermediate Similarity	NPC160651
0.7988	Intermediate Similarity	NPC175964
0.7988	Intermediate Similarity	NPC472652
0.7988	Intermediate Similarity	NPC471169
0.7987	Intermediate Similarity	NPC470999
0.7987	Intermediate Similarity	NPC307401
0.7976	Intermediate Similarity	NPC23387
0.7976	Intermediate Similarity	NPC470875
0.7975	Intermediate Similarity	NPC253201
0.7975	Intermediate Similarity	NPC302054
0.7964	Intermediate Similarity	NPC476197
0.7964	Intermediate Similarity	NPC39986
0.7964	Intermediate Similarity	NPC472773
0.7964	Intermediate Similarity	NPC51568
0.7964	Intermediate Similarity	NPC302369
0.7964	Intermediate Similarity	NPC234660
0.7964	Intermediate Similarity	NPC472139
0.7964	Intermediate Similarity	NPC419
0.7964	Intermediate Similarity	NPC134254
0.7964	Intermediate Similarity	NPC477405
0.7963	Intermediate Similarity	NPC147340
0.7963	Intermediate Similarity	NPC271460
0.7961	Intermediate Similarity	NPC293253
0.7952	Intermediate Similarity	NPC470789
0.795	Intermediate Similarity	NPC470791
0.795	Intermediate Similarity	NPC470790
0.795	Intermediate Similarity	NPC195325
0.7941	Intermediate Similarity	NPC470995
0.7939	Intermediate Similarity	NPC299038
0.7939	Intermediate Similarity	NPC81405
0.7939	Intermediate Similarity	NPC36655
0.7939	Intermediate Similarity	NPC472778
0.7939	Intermediate Similarity	NPC261597
0.7939	Intermediate Similarity	NPC472776

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 NPC1408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	834
0.2-0.3	1905
0.3-0.4	2789
0.4-0.5	2030
0.5-0.6	931
0.6-0.7	305
0.7-0.8	19
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8256	Intermediate Similarity	NPD8434	Phase 2
0.7861	Intermediate Similarity	NPD6764	Approved
0.7861	Intermediate Similarity	NPD6765	Approved
0.7844	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6785	Approved
0.7684	Intermediate Similarity	NPD6784	Approved
0.7427	Intermediate Similarity	NPD919	Approved
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.7341	Intermediate Similarity	NPD1247	Approved
0.7301	Intermediate Similarity	NPD4628	Phase 3
0.7294	Intermediate Similarity	NPD5761	Phase 2
0.7294	Intermediate Similarity	NPD5760	Phase 2
0.7294	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7184	Intermediate Similarity	NPD5494	Approved
0.7169	Intermediate Similarity	NPD6799	Approved
0.7161	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD920	Approved
0.7135	Intermediate Similarity	NPD6801	Discontinued
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7819	Suspended
0.7085	Intermediate Similarity	NPD8404	Phase 2
0.7083	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6559	Discontinued
0.7052	Intermediate Similarity	NPD5402	Approved
0.7024	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5844	Phase 1
0.6966	Remote Similarity	NPD3926	Phase 2
0.6949	Remote Similarity	NPD8127	Discontinued
0.6946	Remote Similarity	NPD3887	Approved
0.6941	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5403	Approved
0.6928	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5401	Approved
0.6915	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3882	Suspended
0.6914	Remote Similarity	NPD4966	Approved
0.6914	Remote Similarity	NPD4965	Approved
0.6914	Remote Similarity	NPD4967	Phase 2
0.6909	Remote Similarity	NPD5762	Approved
0.6909	Remote Similarity	NPD5763	Approved
0.689	Remote Similarity	NPD3748	Approved
0.6882	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD7095	Approved
0.6872	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3226	Approved
0.6851	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2796	Approved
0.6836	Remote Similarity	NPD6234	Discontinued
0.6826	Remote Similarity	NPD1243	Approved
0.6818	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6832	Phase 2
0.6805	Remote Similarity	NPD7236	Approved
0.6796	Remote Similarity	NPD7473	Discontinued
0.6786	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7411	Suspended
0.6763	Remote Similarity	NPD7458	Discontinued
0.6761	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7799	Discontinued
0.6753	Remote Similarity	NPD4107	Approved
0.6748	Remote Similarity	NPD4060	Phase 1
0.6747	Remote Similarity	NPD2438	Suspended
0.6743	Remote Similarity	NPD37	Approved
0.6725	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5585	Approved
0.6707	Remote Similarity	NPD2353	Approved
0.6707	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7239	Suspended
0.6705	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6233	Phase 2
0.6687	Remote Similarity	NPD8032	Phase 2
0.6687	Remote Similarity	NPD2799	Discontinued
0.6686	Remote Similarity	NPD3750	Approved
0.6685	Remote Similarity	NPD3749	Approved
0.6684	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7199	Phase 2
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1934	Approved
0.6648	Remote Similarity	NPD6166	Phase 2
0.6647	Remote Similarity	NPD1551	Phase 2
0.6647	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD3972	Approved
0.6633	Remote Similarity	NPD4482	Phase 3
0.6631	Remote Similarity	NPD8312	Approved
0.6631	Remote Similarity	NPD8313	Approved
0.663	Remote Similarity	NPD6232	Discontinued
0.6629	Remote Similarity	NPD4380	Phase 2
0.6626	Remote Similarity	NPD6798	Discontinued
0.6626	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3266	Approved
0.6625	Remote Similarity	NPD3267	Approved
0.6614	Remote Similarity	NPD8150	Discontinued
0.6613	Remote Similarity	NPD8368	Discontinued
0.6613	Remote Similarity	NPD7251	Discontinued
0.6607	Remote Similarity	NPD2346	Discontinued
0.6592	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4110	Phase 3
0.6578	Remote Similarity	NPD7808	Phase 3
0.6576	Remote Similarity	NPD3751	Discontinued
0.6573	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7435	Discontinued
0.6566	Remote Similarity	NPD7497	Discontinued
0.6559	Remote Similarity	NPD6797	Phase 2
0.6557	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2403	Approved
0.6557	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2354	Approved
0.6548	Remote Similarity	NPD6099	Approved
0.6548	Remote Similarity	NPD6100	Approved
0.6548	Remote Similarity	NPD2935	Discontinued
0.6545	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2979	Phase 3
0.6545	Remote Similarity	NPD4307	Phase 2
0.6541	Remote Similarity	NPD1608	Approved
0.6538	Remote Similarity	NPD6808	Phase 2
0.6538	Remote Similarity	NPD3787	Discontinued
0.6536	Remote Similarity	NPD7768	Phase 2
0.6532	Remote Similarity	NPD2532	Approved
0.6532	Remote Similarity	NPD2533	Approved
0.6532	Remote Similarity	NPD2534	Approved
0.6527	Remote Similarity	NPD7097	Phase 1
0.6524	Remote Similarity	NPD3268	Approved
0.6524	Remote Similarity	NPD7240	Approved
0.6517	Remote Similarity	NPD2801	Approved
0.6509	Remote Similarity	NPD6004	Phase 3
0.6509	Remote Similarity	NPD6005	Phase 3
0.6509	Remote Similarity	NPD6002	Phase 3
0.6509	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7074	Phase 3
0.65	Remote Similarity	NPD4359	Approved
0.6497	Remote Similarity	NPD6385	Approved
0.6497	Remote Similarity	NPD6386	Approved
0.6494	Remote Similarity	NPD5049	Phase 3
0.6491	Remote Similarity	NPD7003	Approved
0.6488	Remote Similarity	NPD7033	Discontinued
0.6486	Remote Similarity	NPD2163	Approved
0.6484	Remote Similarity	NPD6959	Discontinued
0.6471	Remote Similarity	NPD1549	Phase 2
0.6471	Remote Similarity	NPD2897	Discontinued
0.6471	Remote Similarity	NPD4534	Discontinued
0.646	Remote Similarity	NPD1876	Approved
0.6458	Remote Similarity	NPD8435	Approved
0.6456	Remote Similarity	NPD7047	Phase 3
0.6456	Remote Similarity	NPD1778	Approved
0.6452	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7054	Approved
0.6448	Remote Similarity	NPD7229	Phase 3
0.6446	Remote Similarity	NPD4140	Approved
0.6437	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7685	Pre-registration
0.6425	Remote Similarity	NPD8455	Phase 2
0.6425	Remote Similarity	NPD1465	Phase 2
0.6424	Remote Similarity	NPD2313	Discontinued
0.6424	Remote Similarity	NPD3764	Approved
0.6417	Remote Similarity	NPD7472	Approved
0.6413	Remote Similarity	NPD5242	Approved
0.6412	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2344	Approved
0.6407	Remote Similarity	NPD1933	Approved
0.6404	Remote Similarity	NPD6873	Phase 2
0.64	Remote Similarity	NPD1512	Approved
0.6398	Remote Similarity	NPD5327	Phase 3
0.6395	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5691	Approved
0.6391	Remote Similarity	NPD4308	Phase 3
0.6389	Remote Similarity	NPD5353	Approved
0.6386	Remote Similarity	NPD4062	Phase 3
0.6386	Remote Similarity	NPD4870	Approved
0.6381	Remote Similarity	NPD7907	Approved
0.6378	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD1281	Approved
0.6375	Remote Similarity	NPD1611	Approved
0.6375	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5958	Discontinued
0.6373	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8361	Approved
0.6373	Remote Similarity	NPD8360	Approved
0.6373	Remote Similarity	NPD7874	Approved
0.6369	Remote Similarity	NPD9092	Discovery

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