NPASS Compound

Structure

CID88593 OpenBabel06191715422D 45 50 0 0 1 0 0 0 0 0999 V2000 -1.7588 -0.9036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6492 -4.8216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4949 1.7207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5715 1.4150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7927 -2.2781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3461 -3.2275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4256 -3.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3461 -2.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0498 -2.7015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 1.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5051 -3.2275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4256 -1.6332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0470 -3.0109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3338 0.6754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6538 -3.5596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0786 1.1054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9960 -2.5662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3560 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9007 -1.5076 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6014 -4.3805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5051 -2.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8385 0.5372 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0313 -4.0602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7288 0.3198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1270 -3.1780 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9530 -1.3747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2224 -0.5633 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8374 -2.7312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5846 -1.6332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1732 -4.6642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6177 -0.7373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7899 0.7112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9327 -1.6727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0636 -1.0609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4595 -4.9845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5846 -0.5703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2673 -5.7094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0477 -1.0497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0244 -4.3993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1891 0.5855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6955 -3.3353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2211 -4.2231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6642 -2.1646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5780 -0.9583 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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 9 15 2 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 39 1 0 0 0 0 16 40 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 34 1 1 0 0 0 20 35 2 0 0 0 0 20 41 1 0 0 0 0 21 29 1 0 0 0 0 22 18 1 6 0 0 0 22 27 1 0 0 0 0 22 32 1 0 0 0 0 23 30 1 0 0 0 0 23 39 1 0 0 0 0 24 31 1 0 0 0 0 24 40 1 0 0 0 0 25 28 1 0 0 0 0 25 42 1 1 0 0 0 26 33 1 6 0 0 0 26 43 1 0 0 0 0 27 34 1 1 0 0 0 27 44 1 0 0 0 0 28 33 1 1 0 0 0 28 41 1 0 0 0 0 29 36 2 0 0 0 0 29 43 1 0 0 0 0 30 37 2 0 0 0 0 30 42 1 0 0 0 0 31 38 2 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 34 1 1 0 0 0 34 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.23
Volume:	612.973
LogP:	4.851
LogD:	3.539
LogS:	-4.609
# Rotatable Bonds:	11
TPSA:	140.71
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.248
Synthetic Accessibility Score:	5.897
Fsp3:	0.471
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:	-5.008
MDCK Permeability:	3.4118616895284504e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.119
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.51428985595703%
Volume Distribution (VD):	2.286
Pgp-substrate:	6.392251014709473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.38
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.216
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	9.434
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.857
Human Hepatotoxicity (H-HT):	0.927
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.718
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.03
Carcinogencity:	0.168
Eye Corrosion:	0.003
Eye Irritation:	0.422
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC88593

Natural Product ID:	NPC88593
*Common Name:**	Orbiculin F
IUPAC Name:	n.a.
Synonyms:	Orbiculin F
Standard InCHIKey:	WTXHOBPQVWOYDA-LEOXFKOJSA-N
Standard InCHI:	InChI=1S/C34H36O11/c1-19-17-25(42-30(37)23-13-9-15-39-23)28(41-20(2)35)33(5)26(43-29(36)21-11-7-6-8-12-21)18-22-27(34(19,33)45-32(22,3)4)44-31(38)24-14-10-16-40-24/h6-16,19,22,25-28H,17-18H2,1-5H3/t19-,22-,25+,26+,27-,28+,33-,34-/m1/s1
SMILES:	C[C@@H]1C[C@@H]([C@@H]([C@@]2(C)[C@H](C[C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)c1ccco1)OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1ccco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506073
PubChem CID:	10579736
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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	300000.0	nM	PMID[456436]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32400.0	nM	PMID[456437]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39300.0	nM	PMID[456437]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[456437]
NPT2	Others	Unspecified		Ratio IC50	=	35.7	n.a.	PMID[456437]
NPT2	Others	Unspecified		Ratio IC50	=	4.4	n.a.	PMID[456437]
NPT2	Others	Unspecified		Ratio IC50	=	8.9	n.a.	PMID[456437]
NPT2	Others	Unspecified		Ratio IC50	=	11.0	n.a.	PMID[456437]

☑ 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 NPC88593 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	440
0.1-0.2	1577
0.2-0.3	2914
0.3-0.4	6531
0.4-0.5	11569
0.5-0.6	7458
0.6-0.7	9444
0.7-0.8	2481
0.8-0.85	225
0.85-0.9	37
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9682	High Similarity	NPC475039
0.9682	High Similarity	NPC14499
0.9682	High Similarity	NPC476035
0.9427	High Similarity	NPC1408
0.9427	High Similarity	NPC246841
0.9375	High Similarity	NPC159520
0.9136	High Similarity	NPC61967
0.9018	High Similarity	NPC27541
0.9018	High Similarity	NPC62692
0.9018	High Similarity	NPC126984
0.8944	High Similarity	NPC195954
0.8902	High Similarity	NPC276735
0.8841	High Similarity	NPC285567
0.8827	High Similarity	NPC88007
0.8802	High Similarity	NPC118086
0.878	High Similarity	NPC68848
0.878	High Similarity	NPC471003
0.875	High Similarity	NPC475641
0.875	High Similarity	NPC294512
0.875	High Similarity	NPC475237
0.8735	High Similarity	NPC277618
0.8734	High Similarity	NPC71821
0.8727	High Similarity	NPC283209
0.872	High Similarity	NPC191828
0.872	High Similarity	NPC8389
0.8712	High Similarity	NPC194499
0.8712	High Similarity	NPC469847
0.8706	High Similarity	NPC176413
0.8706	High Similarity	NPC56953
0.869	High Similarity	NPC302392
0.8683	High Similarity	NPC310572
0.8667	High Similarity	NPC79571
0.865	High Similarity	NPC104736
0.865	High Similarity	NPC41880
0.8614	High Similarity	NPC469846
0.8598	High Similarity	NPC304692
0.8598	High Similarity	NPC7059
0.8588	High Similarity	NPC469848
0.858	High Similarity	NPC322546
0.858	High Similarity	NPC308205
0.8571	High Similarity	NPC212257
0.8571	High Similarity	NPC270312
0.8571	High Similarity	NPC473753
0.8571	High Similarity	NPC473766
0.8554	High Similarity	NPC188649
0.8521	High Similarity	NPC296558
0.8521	High Similarity	NPC291742
0.8512	High Similarity	NPC86800
0.8512	High Similarity	NPC121995
0.8503	High Similarity	NPC288602
0.8503	High Similarity	NPC88841
0.8497	Intermediate Similarity	NPC11062
0.8488	Intermediate Similarity	NPC167340
0.8466	Intermediate Similarity	NPC29695
0.8466	Intermediate Similarity	NPC182427
0.8466	Intermediate Similarity	NPC121615
0.8466	Intermediate Similarity	NPC294511
0.8457	Intermediate Similarity	NPC228842
0.8452	Intermediate Similarity	NPC56358
0.8443	Intermediate Similarity	NPC470939
0.8443	Intermediate Similarity	NPC18986
0.8402	Intermediate Similarity	NPC308156
0.8402	Intermediate Similarity	NPC472141
0.8393	Intermediate Similarity	NPC471168
0.8385	Intermediate Similarity	NPC255414
0.8383	Intermediate Similarity	NPC287559
0.8373	Intermediate Similarity	NPC214495
0.8373	Intermediate Similarity	NPC470119
0.8373	Intermediate Similarity	NPC167142
0.8373	Intermediate Similarity	NPC472283
0.8365	Intermediate Similarity	NPC470231
0.8364	Intermediate Similarity	NPC476262
0.8354	Intermediate Similarity	NPC472672
0.8353	Intermediate Similarity	NPC476850
0.8353	Intermediate Similarity	NPC476861
0.8333	Intermediate Similarity	NPC470792
0.8333	Intermediate Similarity	NPC471167
0.8333	Intermediate Similarity	NPC471166
0.8323	Intermediate Similarity	NPC473473
0.8323	Intermediate Similarity	NPC473368
0.8323	Intermediate Similarity	NPC475295
0.8313	Intermediate Similarity	NPC107646
0.8305	Intermediate Similarity	NPC105395
0.8304	Intermediate Similarity	NPC160651
0.8304	Intermediate Similarity	NPC271235
0.8303	Intermediate Similarity	NPC253201
0.8303	Intermediate Similarity	NPC237259
0.8303	Intermediate Similarity	NPC302054
0.8303	Intermediate Similarity	NPC98206
0.8303	Intermediate Similarity	NPC34421
0.8294	Intermediate Similarity	NPC475779
0.8293	Intermediate Similarity	NPC116717
0.8293	Intermediate Similarity	NPC18135
0.8284	Intermediate Similarity	NPC476197
0.8282	Intermediate Similarity	NPC69647
0.8282	Intermediate Similarity	NPC471001
0.8282	Intermediate Similarity	NPC125182
0.8274	Intermediate Similarity	NPC305016
0.8274	Intermediate Similarity	NPC475381
0.8274	Intermediate Similarity	NPC472653
0.8263	Intermediate Similarity	NPC475066
0.8263	Intermediate Similarity	NPC286722
0.8253	Intermediate Similarity	NPC25351
0.8246	Intermediate Similarity	NPC472775
0.8246	Intermediate Similarity	NPC472774
0.8242	Intermediate Similarity	NPC476201
0.8242	Intermediate Similarity	NPC268905
0.8235	Intermediate Similarity	NPC476856
0.8235	Intermediate Similarity	NPC476857
0.8235	Intermediate Similarity	NPC469849
0.8235	Intermediate Similarity	NPC476858
0.8235	Intermediate Similarity	NPC123088
0.8229	Intermediate Similarity	NPC472665
0.8225	Intermediate Similarity	NPC329938
0.8225	Intermediate Similarity	NPC82851
0.8221	Intermediate Similarity	NPC254558
0.8217	Intermediate Similarity	NPC307401
0.8214	Intermediate Similarity	NPC474611
0.8214	Intermediate Similarity	NPC475967
0.8214	Intermediate Similarity	NPC472671
0.8214	Intermediate Similarity	NPC237155
0.8214	Intermediate Similarity	NPC475226
0.8204	Intermediate Similarity	NPC126723
0.8204	Intermediate Similarity	NPC209364
0.8202	Intermediate Similarity	NPC247563
0.8202	Intermediate Similarity	NPC242068
0.8199	Intermediate Similarity	NPC471107
0.8199	Intermediate Similarity	NPC471100
0.8198	Intermediate Similarity	NPC255787
0.8198	Intermediate Similarity	NPC472652
0.8198	Intermediate Similarity	NPC327922
0.8187	Intermediate Similarity	NPC470875
0.8182	Intermediate Similarity	NPC291150
0.8182	Intermediate Similarity	NPC240214
0.8176	Intermediate Similarity	NPC469338
0.8176	Intermediate Similarity	NPC472139
0.8176	Intermediate Similarity	NPC134254
0.8176	Intermediate Similarity	NPC39986
0.8176	Intermediate Similarity	NPC302369
0.8176	Intermediate Similarity	NPC292389
0.8176	Intermediate Similarity	NPC472669
0.8166	Intermediate Similarity	NPC25255
0.8155	Intermediate Similarity	NPC470118
0.8155	Intermediate Similarity	NPC81405
0.815	Intermediate Similarity	NPC470995
0.8144	Intermediate Similarity	NPC75310
0.814	Intermediate Similarity	NPC41689
0.814	Intermediate Similarity	NPC173516
0.814	Intermediate Similarity	NPC472282
0.814	Intermediate Similarity	NPC476853
0.814	Intermediate Similarity	NPC476224
0.814	Intermediate Similarity	NPC472651
0.8133	Intermediate Similarity	NPC246164
0.8129	Intermediate Similarity	NPC476860
0.8129	Intermediate Similarity	NPC276551
0.8129	Intermediate Similarity	NPC470940
0.8121	Intermediate Similarity	NPC476122
0.8121	Intermediate Similarity	NPC5180
0.8118	Intermediate Similarity	NPC193798
0.8118	Intermediate Similarity	NPC472771
0.8118	Intermediate Similarity	NPC472668
0.8113	Intermediate Similarity	NPC4341
0.8113	Intermediate Similarity	NPC48017
0.8113	Intermediate Similarity	NPC43241
0.8113	Intermediate Similarity	NPC473758
0.8113	Intermediate Similarity	NPC476094
0.8113	Intermediate Similarity	NPC473112
0.8113	Intermediate Similarity	NPC200592
0.8113	Intermediate Similarity	NPC147880
0.8113	Intermediate Similarity	NPC473613
0.8113	Intermediate Similarity	NPC211137
0.8113	Intermediate Similarity	NPC473081
0.8113	Intermediate Similarity	NPC184747
0.8113	Intermediate Similarity	NPC473109
0.8113	Intermediate Similarity	NPC473060
0.8113	Intermediate Similarity	NPC473085
0.811	Intermediate Similarity	NPC19747
0.811	Intermediate Similarity	NPC470245
0.811	Intermediate Similarity	NPC243165
0.811	Intermediate Similarity	NPC473214
0.8107	Intermediate Similarity	NPC84349
0.8107	Intermediate Similarity	NPC472823
0.8107	Intermediate Similarity	NPC477403
0.8107	Intermediate Similarity	NPC123153
0.8107	Intermediate Similarity	NPC140952
0.8103	Intermediate Similarity	NPC285227
0.8098	Intermediate Similarity	NPC62799
0.8098	Intermediate Similarity	NPC470999
0.8095	Intermediate Similarity	NPC60973
0.8095	Intermediate Similarity	NPC175964
0.8095	Intermediate Similarity	NPC263265
0.8095	Intermediate Similarity	NPC471169
0.8092	Intermediate Similarity	NPC471397
0.809	Intermediate Similarity	NPC473729
0.809	Intermediate Similarity	NPC254588
0.8089	Intermediate Similarity	NPC291638
0.8089	Intermediate Similarity	NPC472577
0.8089	Intermediate Similarity	NPC195647
0.8089	Intermediate Similarity	NPC66761
0.8089	Intermediate Similarity	NPC17877

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 NPC88593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	859
0.2-0.3	1614
0.3-0.4	2761
0.4-0.5	2140
0.5-0.6	1025
0.6-0.7	341
0.7-0.8	42
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8563	High Similarity	NPD8434	Phase 2
0.7953	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6764	Approved
0.7865	Intermediate Similarity	NPD6765	Approved
0.7692	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6785	Approved
0.7692	Intermediate Similarity	NPD6784	Approved
0.7544	Intermediate Similarity	NPD6599	Discontinued
0.7543	Intermediate Similarity	NPD919	Approved
0.7514	Intermediate Similarity	NPD5761	Phase 2
0.7514	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5760	Phase 2
0.7486	Intermediate Similarity	NPD7075	Discontinued
0.7458	Intermediate Similarity	NPD1247	Approved
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7414	Intermediate Similarity	NPD7819	Suspended
0.7403	Intermediate Similarity	NPD5844	Phase 1
0.7401	Intermediate Similarity	NPD5494	Approved
0.7377	Intermediate Similarity	NPD6559	Discontinued
0.7371	Intermediate Similarity	NPD3817	Phase 2
0.7368	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8404	Phase 2
0.736	Intermediate Similarity	NPD8127	Discontinued
0.7356	Intermediate Similarity	NPD6801	Discontinued
0.7349	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6799	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5402	Approved
0.7273	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD920	Approved
0.7232	Intermediate Similarity	NPD4967	Phase 2
0.7232	Intermediate Similarity	NPD4965	Approved
0.7232	Intermediate Similarity	NPD4966	Approved
0.7232	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD7411	Suspended
0.7198	Intermediate Similarity	NPD7473	Discontinued
0.7184	Intermediate Similarity	NPD3226	Approved
0.7182	Intermediate Similarity	NPD3926	Phase 2
0.7168	Intermediate Similarity	NPD5403	Approved
0.7158	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7799	Discontinued
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7151	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6234	Discontinued
0.7151	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5401	Approved
0.7135	Intermediate Similarity	NPD7236	Approved
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8032	Phase 2
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD3748	Approved
0.7112	Intermediate Similarity	NPD8313	Approved
0.7112	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD3749	Approved
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7083	Intermediate Similarity	NPD2796	Approved
0.7076	Intermediate Similarity	NPD3887	Approved
0.7073	Intermediate Similarity	NPD6798	Discontinued
0.7072	Intermediate Similarity	NPD7199	Phase 2
0.7062	Intermediate Similarity	NPD37	Approved
0.7049	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6166	Phase 2
0.7049	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3882	Suspended
0.7039	Intermediate Similarity	NPD7768	Phase 2
0.7033	Intermediate Similarity	NPD6232	Discontinued
0.7029	Intermediate Similarity	NPD7239	Suspended
0.7027	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7095	Approved
0.7011	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8150	Discontinued
0.6994	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8407	Phase 2
0.6983	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6190	Approved
0.6973	Remote Similarity	NPD7228	Approved
0.6959	Remote Similarity	NPD1243	Approved
0.6954	Remote Similarity	NPD4107	Approved
0.6954	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6832	Phase 2
0.6927	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8455	Phase 2
0.6919	Remote Similarity	NPD7003	Approved
0.6919	Remote Similarity	NPD3750	Approved
0.6915	Remote Similarity	NPD8368	Discontinued
0.6885	Remote Similarity	NPD6959	Discontinued
0.6882	Remote Similarity	NPD3818	Discontinued
0.6882	Remote Similarity	NPD2438	Suspended
0.6882	Remote Similarity	NPD3751	Discontinued
0.6878	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7808	Phase 3
0.6872	Remote Similarity	NPD1934	Approved
0.6871	Remote Similarity	NPD3266	Approved
0.6871	Remote Similarity	NPD3267	Approved
0.6867	Remote Similarity	NPD3764	Approved
0.6865	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4380	Phase 2
0.685	Remote Similarity	NPD7497	Discontinued
0.685	Remote Similarity	NPD7435	Discontinued
0.6848	Remote Similarity	NPD7229	Phase 3
0.6848	Remote Similarity	NPD3787	Discontinued
0.6842	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2353	Approved
0.6842	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD5763	Approved
0.6842	Remote Similarity	NPD5762	Approved
0.6839	Remote Similarity	NPD8435	Approved
0.6834	Remote Similarity	NPD4482	Phase 3
0.6825	Remote Similarity	NPD7251	Discontinued
0.6825	Remote Similarity	NPD7240	Approved
0.6824	Remote Similarity	NPD2799	Discontinued
0.6813	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD17	Approved
0.679	Remote Similarity	NPD3972	Approved
0.6786	Remote Similarity	NPD4307	Phase 2
0.6784	Remote Similarity	NPD1551	Phase 2
0.6784	Remote Similarity	NPD6099	Approved
0.6784	Remote Similarity	NPD6100	Approved
0.6772	Remote Similarity	NPD6797	Phase 2
0.6768	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3268	Approved
0.6757	Remote Similarity	NPD6808	Phase 2
0.6755	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD8361	Approved
0.6753	Remote Similarity	NPD8360	Approved
0.674	Remote Similarity	NPD2801	Approved
0.6737	Remote Similarity	NPD7685	Pre-registration
0.6736	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD8285	Discontinued
0.6733	Remote Similarity	NPD7871	Phase 2
0.6733	Remote Similarity	NPD7870	Phase 2
0.6732	Remote Similarity	NPD7874	Approved
0.6732	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4110	Phase 3
0.6724	Remote Similarity	NPD8166	Discontinued
0.6724	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7074	Phase 3
0.6717	Remote Similarity	NPD8485	Approved
0.6717	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2897	Discontinued
0.6705	Remote Similarity	NPD1549	Phase 2
0.6687	Remote Similarity	NPD1608	Approved
0.6686	Remote Similarity	NPD2354	Approved
0.6686	Remote Similarity	NPD4060	Phase 1
0.6686	Remote Similarity	NPD2935	Discontinued
0.6686	Remote Similarity	NPD2979	Phase 3
0.6684	Remote Similarity	NPD2403	Approved
0.6683	Remote Similarity	NPD7696	Phase 3
0.6683	Remote Similarity	NPD7698	Approved
0.6683	Remote Similarity	NPD7697	Approved
0.6683	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD7058	Phase 2
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD7054	Approved
0.6651	Remote Similarity	NPD7907	Approved
0.6648	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD6002	Phase 3
0.6647	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6004	Phase 3
0.6647	Remote Similarity	NPD6005	Phase 3
0.6647	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2344	Approved
0.6647	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1933	Approved
0.6647	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5585	Approved
0.6632	Remote Similarity	NPD7472	Approved
0.663	Remote Similarity	NPD6386	Approved
0.663	Remote Similarity	NPD6385	Approved
0.6629	Remote Similarity	NPD5049	Phase 3
0.6629	Remote Similarity	NPD1512	Approved
0.6628	Remote Similarity	NPD4308	Phase 3
0.6628	Remote Similarity	NPD7033	Discontinued
0.6626	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6778	Approved
0.6617	Remote Similarity	NPD6780	Approved
0.6617	Remote Similarity	NPD6776	Approved
0.6617	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6782	Approved
0.6617	Remote Similarity	NPD6781	Approved
0.6617	Remote Similarity	NPD6777	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