NPASS Compound

Structure

CID159520 OpenBabel06191715532D 44 49 0 0 1 0 0 0 0 0999 V2000 -0.7349 -1.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1643 2.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2248 -0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7147 0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7147 2.1214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6520 -0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7528 4.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8727 0.6366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7201 -1.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8209 4.6112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6690 -0.3219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6520 0.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7528 3.3286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0242 1.1265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2046 -0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2450 2.1214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -0.4243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6744 2.1214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7349 1.2728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1441 -0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2450 3.8185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6946 -0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6946 0.4243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7349 2.1214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2450 0.4243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2046 1.2728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1643 -0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7349 3.8185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2046 -1.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7349 0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 1.2728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7349 0.4243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1643 1.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6744 -1.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 4.6671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6946 -2.1214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7201 0.3684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8209 3.0258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2960 0.4708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6946 2.1214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6744 0.4243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 2.9700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2248 -1.2728 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 20 2 0 0 0 0 10 21 2 0 0 0 0 11 22 2 0 0 0 0 12 37 1 0 0 0 0 13 38 1 0 0 0 0 14 39 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 32 1 6 0 0 0 18 33 2 0 0 0 0 18 40 1 0 0 0 0 19 16 1 1 0 0 0 19 25 1 0 0 0 0 19 30 1 0 0 0 0 20 27 1 0 0 0 0 20 37 1 0 0 0 0 21 28 1 0 0 0 0 21 38 1 0 0 0 0 22 29 1 0 0 0 0 22 39 1 0 0 0 0 23 26 1 0 0 0 0 23 41 1 6 0 0 0 24 31 1 1 0 0 0 24 42 1 0 0 0 0 25 32 1 1 0 0 0 25 43 1 0 0 0 0 26 31 1 6 0 0 0 26 40 1 0 0 0 0 27 34 2 0 0 0 0 27 41 1 0 0 0 0 28 35 2 0 0 0 0 28 42 1 0 0 0 0 29 36 2 0 0 0 0 29 43 1 0 0 0 0 30 44 1 0 0 0 0 31 32 1 6 0 0 0 32 44 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.21
Volume:	589.807
LogP:	4.342
LogD:	2.904
LogS:	-4.523
# Rotatable Bonds:	11
TPSA:	153.85
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	6.051
Fsp3:	0.5
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:	-4.906
MDCK Permeability:	4.0205875848187134e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.499
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	85.88150787353516%
Volume Distribution (VD):	2.684
Pgp-substrate:	5.385729789733887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.331
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.201
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.747
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	9.544
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.883
Human Hepatotoxicity (H-HT):	0.909
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.022
Carcinogencity:	0.173
Eye Corrosion:	0.003
Eye Irritation:	0.373
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC159520

Natural Product ID:	NPC159520
*Common Name:**	Orbiculin I
IUPAC Name:	n.a.
Synonyms:	orbiculin I
Standard InCHIKey:	LKGNMDBWGMJTKM-BXAUWJRVSA-N
Standard InCHI:	InChI=1S/C32H34O12/c1-17-15-23(41-27(34)20-9-6-12-37-20)26(40-18(2)33)31(5)24(42-28(35)21-10-7-13-38-21)16-19-25(32(17,31)44-30(19,3)4)43-29(36)22-11-8-14-39-22/h6-14,17,19,23-26H,15-16H2,1-5H3/t17-,19-,23+,24+,25-,26+,31-,32-/m1/s1
SMILES:	CC(=O)O[C@H]1[C@@H](OC(=O)c2ccco2)C[C@H]([C@@]23[C@]1(C)[C@@H](OC(=O)c1ccco1)C[C@H]([C@H]3OC(=O)c1ccco1)C(O2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505566
PubChem CID:	11050329
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.	n.a.	n.a.	PMID[10346948]
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[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.	n.a.	n.a.	PMID[9461657]
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.	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	51200.0	nM	PMID[534842]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	61500.0	nM	PMID[534842]

☑ 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 NPC159520 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	419
0.1-0.2	1496
0.2-0.3	3169
0.3-0.4	7126
0.4-0.5	11941
0.5-0.6	7810
0.6-0.7	9431
0.7-0.8	1164
0.8-0.85	108
0.85-0.9	24
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9673	High Similarity	NPC246841
0.9673	High Similarity	NPC1408
0.9375	High Similarity	NPC88593
0.9062	High Similarity	NPC14499
0.9062	High Similarity	NPC476035
0.9062	High Similarity	NPC475039
0.8659	High Similarity	NPC61967
0.8476	Intermediate Similarity	NPC191828
0.8466	Intermediate Similarity	NPC195954
0.8447	Intermediate Similarity	NPC308205
0.8447	Intermediate Similarity	NPC322546
0.8434	Intermediate Similarity	NPC126984
0.8434	Intermediate Similarity	NPC27541
0.8434	Intermediate Similarity	NPC62692
0.8373	Intermediate Similarity	NPC285567
0.8354	Intermediate Similarity	NPC88007
0.8323	Intermediate Similarity	NPC276735
0.8313	Intermediate Similarity	NPC68848
0.8263	Intermediate Similarity	NPC283209
0.825	Intermediate Similarity	NPC71821
0.8242	Intermediate Similarity	NPC470119
0.8242	Intermediate Similarity	NPC194499
0.8242	Intermediate Similarity	NPC214495
0.8242	Intermediate Similarity	NPC469847
0.8235	Intermediate Similarity	NPC118086
0.8225	Intermediate Similarity	NPC473766
0.8225	Intermediate Similarity	NPC473753
0.8221	Intermediate Similarity	NPC29695
0.8221	Intermediate Similarity	NPC182427
0.8204	Intermediate Similarity	NPC471003
0.8193	Intermediate Similarity	NPC473368
0.8187	Intermediate Similarity	NPC294512
0.8187	Intermediate Similarity	NPC475641
0.8187	Intermediate Similarity	NPC475237
0.8182	Intermediate Similarity	NPC104736
0.8182	Intermediate Similarity	NPC41880
0.8166	Intermediate Similarity	NPC86800
0.8166	Intermediate Similarity	NPC277618
0.8155	Intermediate Similarity	NPC469846
0.8155	Intermediate Similarity	NPC471168
0.815	Intermediate Similarity	NPC56953
0.815	Intermediate Similarity	NPC176413
0.8144	Intermediate Similarity	NPC8389
0.814	Intermediate Similarity	NPC469848
0.8137	Intermediate Similarity	NPC255414
0.8133	Intermediate Similarity	NPC304692
0.8129	Intermediate Similarity	NPC302392
0.8118	Intermediate Similarity	NPC310572
0.8118	Intermediate Similarity	NPC270312
0.8098	Intermediate Similarity	NPC212257
0.8095	Intermediate Similarity	NPC188649
0.8095	Intermediate Similarity	NPC471166
0.8095	Intermediate Similarity	NPC471167
0.8095	Intermediate Similarity	NPC79571
0.8059	Intermediate Similarity	NPC475779
0.8059	Intermediate Similarity	NPC472141
0.8059	Intermediate Similarity	NPC121995
0.8049	Intermediate Similarity	NPC291150
0.8049	Intermediate Similarity	NPC116717
0.8049	Intermediate Similarity	NPC18135
0.8047	Intermediate Similarity	NPC288602
0.8047	Intermediate Similarity	NPC88841
0.8037	Intermediate Similarity	NPC125182
0.8037	Intermediate Similarity	NPC69647
0.8024	Intermediate Similarity	NPC7059
0.8024	Intermediate Similarity	NPC472283
0.8024	Intermediate Similarity	NPC475066
0.8024	Intermediate Similarity	NPC167142
0.8012	Intermediate Similarity	NPC476861
0.8012	Intermediate Similarity	NPC476262
0.8012	Intermediate Similarity	NPC476850
0.8	Intermediate Similarity	NPC56358
0.8	Intermediate Similarity	NPC294511
0.8	Intermediate Similarity	NPC268905
0.8	Intermediate Similarity	NPC121615
0.7988	Intermediate Similarity	NPC228842
0.7988	Intermediate Similarity	NPC5180
0.7988	Intermediate Similarity	NPC470939
0.7988	Intermediate Similarity	NPC18986
0.7977	Intermediate Similarity	NPC285227
0.7976	Intermediate Similarity	NPC472671
0.7976	Intermediate Similarity	NPC473473
0.7976	Intermediate Similarity	NPC475295
0.7976	Intermediate Similarity	NPC475226
0.7965	Intermediate Similarity	NPC291742
0.7965	Intermediate Similarity	NPC296558
0.7955	Intermediate Similarity	NPC11062
0.7943	Intermediate Similarity	NPC167340
0.7941	Intermediate Similarity	NPC472669
0.7939	Intermediate Similarity	NPC240214
0.7929	Intermediate Similarity	NPC287559
0.7929	Intermediate Similarity	NPC305016
0.7929	Intermediate Similarity	NPC472653
0.7927	Intermediate Similarity	NPC471001
0.7917	Intermediate Similarity	NPC470118
0.7917	Intermediate Similarity	NPC286722
0.7907	Intermediate Similarity	NPC476224
0.7907	Intermediate Similarity	NPC472774
0.7907	Intermediate Similarity	NPC472775
0.7904	Intermediate Similarity	NPC75310
0.7898	Intermediate Similarity	NPC472665
0.7895	Intermediate Similarity	NPC469849
0.7895	Intermediate Similarity	NPC476858
0.7895	Intermediate Similarity	NPC476856
0.7895	Intermediate Similarity	NPC123088
0.7895	Intermediate Similarity	NPC476857
0.7892	Intermediate Similarity	NPC476201
0.7892	Intermediate Similarity	NPC472672
0.7882	Intermediate Similarity	NPC82851
0.7882	Intermediate Similarity	NPC472668
0.7882	Intermediate Similarity	NPC329938
0.7882	Intermediate Similarity	NPC470792
0.7877	Intermediate Similarity	NPC105395
0.7877	Intermediate Similarity	NPC242068
0.7877	Intermediate Similarity	NPC247563
0.787	Intermediate Similarity	NPC475967
0.787	Intermediate Similarity	NPC237155
0.787	Intermediate Similarity	NPC84349
0.7866	Intermediate Similarity	NPC243165
0.7866	Intermediate Similarity	NPC19747
0.7861	Intermediate Similarity	NPC327922
0.7861	Intermediate Similarity	NPC271235
0.7861	Intermediate Similarity	NPC472652
0.7861	Intermediate Similarity	NPC160651
0.7857	Intermediate Similarity	NPC175964
0.7857	Intermediate Similarity	NPC126723
0.7857	Intermediate Similarity	NPC209364
0.7857	Intermediate Similarity	NPC471169
0.7857	Intermediate Similarity	NPC107646
0.7853	Intermediate Similarity	NPC62799
0.7849	Intermediate Similarity	NPC470875
0.7849	Intermediate Similarity	NPC308156
0.7844	Intermediate Similarity	NPC98206
0.7844	Intermediate Similarity	NPC34421
0.7844	Intermediate Similarity	NPC253201
0.7844	Intermediate Similarity	NPC237259
0.7844	Intermediate Similarity	NPC302054
0.784	Intermediate Similarity	NPC84479
0.784	Intermediate Similarity	NPC251865
0.7836	Intermediate Similarity	NPC472139
0.7836	Intermediate Similarity	NPC469338
0.7836	Intermediate Similarity	NPC476197
0.7836	Intermediate Similarity	NPC292389
0.7826	Intermediate Similarity	NPC121158
0.7824	Intermediate Similarity	NPC475381
0.7824	Intermediate Similarity	NPC25255
0.7824	Intermediate Similarity	NPC470789
0.7818	Intermediate Similarity	NPC211625
0.7818	Intermediate Similarity	NPC470791
0.7818	Intermediate Similarity	NPC470790
0.7811	Intermediate Similarity	NPC197137
0.7805	Intermediate Similarity	NPC221809
0.7803	Intermediate Similarity	NPC472651
0.7803	Intermediate Similarity	NPC476853
0.7803	Intermediate Similarity	NPC173516
0.7798	Intermediate Similarity	NPC471175
0.7791	Intermediate Similarity	NPC476860
0.7791	Intermediate Similarity	NPC56731
0.7791	Intermediate Similarity	NPC34056
0.7791	Intermediate Similarity	NPC5676
0.7791	Intermediate Similarity	NPC470940
0.7791	Intermediate Similarity	NPC261184
0.7791	Intermediate Similarity	NPC276551
0.7784	Intermediate Similarity	NPC475777
0.7784	Intermediate Similarity	NPC246164
0.7778	Intermediate Similarity	NPC205071
0.7778	Intermediate Similarity	NPC193798
0.7778	Intermediate Similarity	NPC470231
0.7778	Intermediate Similarity	NPC22248
0.7778	Intermediate Similarity	NPC472771
0.7771	Intermediate Similarity	NPC476122
0.7771	Intermediate Similarity	NPC6815
0.7771	Intermediate Similarity	NPC294803
0.7771	Intermediate Similarity	NPC156189
0.7765	Intermediate Similarity	NPC477403
0.7765	Intermediate Similarity	NPC474611
0.7764	Intermediate Similarity	NPC20500
0.7759	Intermediate Similarity	NPC471397
0.7751	Intermediate Similarity	NPC60973
0.7751	Intermediate Similarity	NPC263265
0.7746	Intermediate Similarity	NPC472670
0.7746	Intermediate Similarity	NPC23387
0.7746	Intermediate Similarity	NPC307781
0.7744	Intermediate Similarity	NPC470999
0.7736	Intermediate Similarity	NPC307401
0.7733	Intermediate Similarity	NPC39986
0.7733	Intermediate Similarity	NPC302369
0.7733	Intermediate Similarity	NPC419
0.7733	Intermediate Similarity	NPC234660
0.7733	Intermediate Similarity	NPC51568
0.7733	Intermediate Similarity	NPC477405
0.7733	Intermediate Similarity	NPC134254
0.7733	Intermediate Similarity	NPC472773
0.7725	Intermediate Similarity	NPC147340
0.7725	Intermediate Similarity	NPC271460
0.7714	Intermediate Similarity	NPC470995
0.7711	Intermediate Similarity	NPC195325
0.7709	Intermediate Similarity	NPC470938
0.7707	Intermediate Similarity	NPC293253
0.7706	Intermediate Similarity	NPC472777

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 NPC159520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	858
0.2-0.3	1934
0.3-0.4	2858
0.4-0.5	2005
0.5-0.6	873
0.6-0.7	266
0.7-0.8	13
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
0.8125	Intermediate Similarity	NPD8434	Phase 2
0.764	Intermediate Similarity	NPD6764	Approved
0.764	Intermediate Similarity	NPD6765	Approved
0.7616	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6785	Approved
0.7473	Intermediate Similarity	NPD6784	Approved
0.7216	Intermediate Similarity	NPD919	Approved
0.7209	Intermediate Similarity	NPD6599	Discontinued
0.7189	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1247	Approved
0.7086	Intermediate Similarity	NPD5760	Phase 2
0.7086	Intermediate Similarity	NPD5761	Phase 2
0.7086	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7062	Intermediate Similarity	NPD7075	Discontinued
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.6995	Remote Similarity	NPD8404	Phase 2
0.6989	Remote Similarity	NPD7819	Suspended
0.6983	Remote Similarity	NPD5494	Approved
0.6973	Remote Similarity	NPD6559	Discontinued
0.6959	Remote Similarity	NPD6799	Approved
0.6949	Remote Similarity	NPD3817	Phase 2
0.6937	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD920	Approved
0.6932	Remote Similarity	NPD6801	Discontinued
0.6902	Remote Similarity	NPD5844	Phase 1
0.6879	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3926	Phase 2
0.6854	Remote Similarity	NPD5402	Approved
0.6851	Remote Similarity	NPD8127	Discontinued
0.6848	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6355	Discontinued
0.6802	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3887	Approved
0.6743	Remote Similarity	NPD5403	Approved
0.6724	Remote Similarity	NPD5401	Approved
0.6722	Remote Similarity	NPD4966	Approved
0.6722	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4965	Approved
0.6722	Remote Similarity	NPD3882	Suspended
0.6722	Remote Similarity	NPD4967	Phase 2
0.6706	Remote Similarity	NPD5763	Approved
0.6706	Remote Similarity	NPD5762	Approved
0.6703	Remote Similarity	NPD7473	Discontinued
0.6686	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD3748	Approved
0.6685	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD7799	Discontinued
0.6667	Remote Similarity	NPD3226	Approved
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6234	Discontinued
0.6647	Remote Similarity	NPD2796	Approved
0.6632	Remote Similarity	NPD8312	Approved
0.6632	Remote Similarity	NPD8313	Approved
0.6631	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1243	Approved
0.6609	Remote Similarity	NPD7236	Approved
0.6606	Remote Similarity	NPD6832	Phase 2
0.6597	Remote Similarity	NPD8407	Phase 2
0.6593	Remote Similarity	NPD3749	Approved
0.659	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6233	Phase 2
0.6587	Remote Similarity	NPD8032	Phase 2
0.6583	Remote Similarity	NPD4107	Approved
0.6576	Remote Similarity	NPD7199	Phase 2
0.6573	Remote Similarity	NPD7458	Discontinued
0.6559	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6166	Phase 2
0.6556	Remote Similarity	NPD37	Approved
0.655	Remote Similarity	NPD2438	Suspended
0.6548	Remote Similarity	NPD4060	Phase 1
0.6546	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6232	Discontinued
0.6538	Remote Similarity	NPD7768	Phase 2
0.6534	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8150	Discontinued
0.6527	Remote Similarity	NPD6798	Discontinued
0.6526	Remote Similarity	NPD8368	Discontinued
0.6519	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7239	Suspended
0.6512	Remote Similarity	NPD2353	Approved
0.6512	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5585	Approved
0.6494	Remote Similarity	NPD3750	Approved
0.6492	Remote Similarity	NPD7808	Phase 3
0.6492	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2799	Discontinued
0.6489	Remote Similarity	NPD3818	Discontinued
0.6489	Remote Similarity	NPD7228	Approved
0.6484	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD4482	Phase 3
0.6464	Remote Similarity	NPD1934	Approved
0.646	Remote Similarity	NPD17	Approved
0.6457	Remote Similarity	NPD6190	Approved
0.6453	Remote Similarity	NPD1551	Phase 2
0.6452	Remote Similarity	NPD6808	Phase 2
0.6444	Remote Similarity	NPD4380	Phase 2
0.6442	Remote Similarity	NPD3972	Approved
0.644	Remote Similarity	NPD7251	Discontinued
0.6429	Remote Similarity	NPD8455	Phase 2
0.6429	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3267	Approved
0.6424	Remote Similarity	NPD3266	Approved
0.6416	Remote Similarity	NPD2346	Discontinued
0.6413	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7435	Discontinued
0.6404	Remote Similarity	NPD7497	Discontinued
0.6402	Remote Similarity	NPD3751	Discontinued
0.64	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7003	Approved
0.64	Remote Similarity	NPD4110	Phase 3
0.6398	Remote Similarity	NPD6959	Discontinued
0.6387	Remote Similarity	NPD6797	Phase 2
0.6383	Remote Similarity	NPD2403	Approved
0.6378	Remote Similarity	NPD8435	Approved
0.6368	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3787	Discontinued
0.6364	Remote Similarity	NPD2354	Approved
0.6364	Remote Similarity	NPD7229	Phase 3
0.6358	Remote Similarity	NPD6100	Approved
0.6358	Remote Similarity	NPD2935	Discontinued
0.6358	Remote Similarity	NPD6099	Approved
0.6354	Remote Similarity	NPD7685	Pre-registration
0.6354	Remote Similarity	NPD7240	Approved
0.6353	Remote Similarity	NPD4307	Phase 2
0.6353	Remote Similarity	NPD2979	Phase 3
0.6348	Remote Similarity	NPD2534	Approved
0.6348	Remote Similarity	NPD2533	Approved
0.6348	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2532	Approved
0.6341	Remote Similarity	NPD1608	Approved
0.6339	Remote Similarity	NPD2801	Approved
0.6337	Remote Similarity	NPD7097	Phase 1
0.6335	Remote Similarity	NPD7074	Phase 3
0.6331	Remote Similarity	NPD3268	Approved
0.6331	Remote Similarity	NPD3764	Approved
0.6322	Remote Similarity	NPD6005	Phase 3
0.6322	Remote Similarity	NPD6002	Phase 3
0.6322	Remote Similarity	NPD2344	Approved
0.6322	Remote Similarity	NPD6004	Phase 3
0.6322	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6386	Approved
0.6319	Remote Similarity	NPD6385	Approved
0.6316	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2163	Approved
0.6313	Remote Similarity	NPD5049	Phase 3
0.6308	Remote Similarity	NPD7907	Approved
0.6307	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4359	Approved
0.6303	Remote Similarity	NPD7047	Phase 3
0.6301	Remote Similarity	NPD7033	Discontinued
0.6298	Remote Similarity	NPD7874	Approved
0.6298	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD8360	Approved
0.6294	Remote Similarity	NPD8361	Approved
0.6293	Remote Similarity	NPD7870	Phase 2
0.6293	Remote Similarity	NPD7871	Phase 2
0.6287	Remote Similarity	NPD8285	Discontinued
0.6286	Remote Similarity	NPD4534	Discontinued
0.6286	Remote Similarity	NPD1549	Phase 2
0.6286	Remote Similarity	NPD2897	Discontinued
0.6283	Remote Similarity	NPD7054	Approved
0.6276	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD8485	Approved
0.6269	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD1876	Approved
0.6258	Remote Similarity	NPD1778	Approved
0.6257	Remote Similarity	NPD4140	Approved
0.625	Remote Similarity	NPD1465	Phase 2
0.625	Remote Similarity	NPD7472	Approved
0.6244	Remote Similarity	NPD7680	Approved
0.6244	Remote Similarity	NPD7697	Approved
0.6244	Remote Similarity	NPD7696	Phase 3
0.6244	Remote Similarity	NPD7698	Approved
0.6243	Remote Similarity	NPD5242	Approved
0.6235	Remote Similarity	NPD2313	Discontinued
0.623	Remote Similarity	NPD6873	Phase 2
0.6229	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD1512	Approved
0.6221	Remote Similarity	NPD1933	Approved
0.6216	Remote Similarity	NPD5353	Approved
0.6215	Remote Similarity	NPD8166	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