NPASS Compound

Structure

CID88841 OpenBabel06191715422D 35 38 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 23 1 0 0 0 0 11 32 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 27 2 0 0 0 0 13 33 1 0 0 0 0 14 28 2 0 0 0 0 14 34 1 0 0 0 0 15 29 2 0 0 0 0 15 35 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 6 0 0 0 18 32 1 0 0 0 0 19 24 1 1 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 1 0 0 0 21 22 1 0 0 0 0 21 34 1 6 0 0 0 22 26 1 1 0 0 0 22 35 1 0 0 0 0 23 26 1 0 0 0 0 24 26 1 6 0 0 0 25 7 1 1 0 0 0 25 30 1 0 0 0 0 26 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	489.956
LogP:	2.747
LogD:	2.163
LogS:	-4.085
# Rotatable Bonds:	6
TPSA:	132.5
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	5.063
Fsp3:	0.731
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:	-5.149
MDCK Permeability:	5.010252425563522e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.248
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.781

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.863
Plasma Protein Binding (PPB):	67.30931854248047%
Volume Distribution (VD):	1.765
Pgp-substrate:	25.642934799194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.16
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.113
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	2.62
Half-life (T1/2):	0.295

ADMET: Toxicity

hERG Blockers:	0.504
Human Hepatotoxicity (H-HT):	0.832
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.864
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.244
Carcinogencity:	0.605
Eye Corrosion:	0.009
Eye Irritation:	0.012
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC88841

Natural Product ID:	NPC88841
*Common Name:**	Caesalmin E
IUPAC Name:	[(1S,4aR,5S,6R,6aS,7S,11aS,11bS)-5,6-diacetyloxy-4a,7-dihydroxy-4,4,7,11b-tetramethyl-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-1-yl] acetate
Synonyms:	caesalmin E
Standard InCHIKey:	ZMDJQZBKCANBDV-GZEDFXFRSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-13(27)33-19-8-10-23(4,5)26(31)22(35-15(3)29)21(34-14(2)28)20-17(24(19,26)6)12-18-16(9-11-32-18)25(20,7)30/h9,11,17,19-22,30-31H,8,10,12H2,1-7H3/t17-,19-,20-,21+,22-,24-,25+,26+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H]2[C@H](Cc3c([C@@]2(C)O)cco3)[C@@]2([C@]([C@H]1OC(=O)C)(O)C(C)(C)CC[C@@H]2OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517323
PubChem CID:	10480816
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678648]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[23806110]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24303808]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11853	Eucalyptus froggattii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7886	Eria tomentosa	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13248	Pistacia mexicana	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14392	Caesalpinia minax	Species	Fabaceae	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	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	IC50	=	10.3	ug.mL-1	PMID[553258]
NPT27	Others	Unspecified		LC50	=	165.0	ug.mL-1	PMID[553258]
NPT27	Others	Unspecified		TI	=	16.0	n.a.	PMID[553258]

☑ 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 NPC88841 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	1319
0.2-0.3	2765
0.3-0.4	5399
0.4-0.5	9905
0.5-0.6	8213
0.6-0.7	6033
0.7-0.8	8001
0.8-0.85	496
0.85-0.9	177
0.9-0.95	32
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC288602
0.9934	High Similarity	NPC188649
0.9618	High Similarity	NPC296558
0.9608	High Similarity	NPC88007
0.9548	High Similarity	NPC68848
0.949	High Similarity	NPC121995
0.9481	High Similarity	NPC194499
0.9481	High Similarity	NPC195954
0.943	High Similarity	NPC270312
0.9423	High Similarity	NPC18986
0.9363	High Similarity	NPC285567
0.9359	High Similarity	NPC287559
0.9304	High Similarity	NPC56358
0.9295	High Similarity	NPC474611
0.929	High Similarity	NPC41880
0.9241	High Similarity	NPC283209
0.9236	High Similarity	NPC8389
0.9221	High Similarity	NPC121615
0.9221	High Similarity	NPC294511
0.9216	High Similarity	NPC228842
0.9216	High Similarity	NPC212257
0.9177	High Similarity	NPC79571
0.9177	High Similarity	NPC200782
0.9177	High Similarity	NPC82851
0.915	High Similarity	NPC211625
0.9136	High Similarity	NPC294512
0.9119	High Similarity	NPC472773
0.9108	High Similarity	NPC81405
0.9108	High Similarity	NPC7059
0.9062	High Similarity	NPC470182
0.9062	High Similarity	NPC470940
0.9057	High Similarity	NPC472771
0.9057	High Similarity	NPC329938
0.9051	High Similarity	NPC140952
0.9045	High Similarity	NPC104736
0.9038	High Similarity	NPC114880
0.9038	High Similarity	NPC282445
0.902	High Similarity	NPC71821
0.9018	High Similarity	NPC475641
0.9018	High Similarity	NPC475237
0.9012	High Similarity	NPC160651
0.9006	High Similarity	NPC86800
0.9006	High Similarity	NPC277618
0.9	High Similarity	NPC469338
0.9	High Similarity	NPC292389
0.8987	High Similarity	NPC472776
0.8987	High Similarity	NPC299038
0.8987	High Similarity	NPC472777
0.8987	High Similarity	NPC304692
0.8987	High Similarity	NPC472778
0.8987	High Similarity	NPC249021
0.8981	High Similarity	NPC264943
0.8974	High Similarity	NPC476201
0.897	High Similarity	NPC56953
0.897	High Similarity	NPC176413
0.8951	High Similarity	NPC173516
0.8951	High Similarity	NPC472774
0.8951	High Similarity	NPC472775
0.8944	High Similarity	NPC469849
0.8944	High Similarity	NPC276551
0.8944	High Similarity	NPC276735
0.8931	High Similarity	NPC475967
0.8916	High Similarity	NPC472665
0.8903	High Similarity	NPC69647
0.8903	High Similarity	NPC125182
0.8896	High Similarity	NPC271235
0.8896	High Similarity	NPC255414
0.8896	High Similarity	NPC471397
0.8896	High Similarity	NPC291742
0.8896	High Similarity	NPC255787
0.8889	High Similarity	NPC470875
0.8889	High Similarity	NPC472141
0.8889	High Similarity	NPC475779
0.8882	High Similarity	NPC302369
0.8882	High Similarity	NPC39986
0.8882	High Similarity	NPC477405
0.8882	High Similarity	NPC134254
0.8875	High Similarity	NPC472653
0.8875	High Similarity	NPC477402
0.8868	High Similarity	NPC261597
0.8868	High Similarity	NPC36655
0.8868	High Similarity	NPC167142
0.8868	High Similarity	NPC472772
0.8861	High Similarity	NPC476262
0.8854	High Similarity	NPC469503
0.8839	High Similarity	NPC19747
0.8834	High Similarity	NPC472282
0.8834	High Similarity	NPC473766
0.8834	High Similarity	NPC473753
0.8831	High Similarity	NPC62799
0.882	High Similarity	NPC193798
0.882	High Similarity	NPC263432
0.882	High Similarity	NPC470792
0.882	High Similarity	NPC69028
0.8812	High Similarity	NPC477403
0.8812	High Similarity	NPC307383
0.8805	High Similarity	NPC469485
0.8797	High Similarity	NPC30222
0.879	High Similarity	NPC18135
0.8773	High Similarity	NPC93172
0.8773	High Similarity	NPC97574
0.8773	High Similarity	NPC308156
0.8765	High Similarity	NPC14499
0.8765	High Similarity	NPC475039
0.8765	High Similarity	NPC476197
0.8765	High Similarity	NPC472139
0.8765	High Similarity	NPC476035
0.8758	High Similarity	NPC335761
0.8758	High Similarity	NPC25255
0.875	High Similarity	NPC45101
0.875	High Similarity	NPC173544
0.8742	High Similarity	NPC214541
0.8742	High Similarity	NPC35000
0.8742	High Similarity	NPC44675
0.8742	High Similarity	NPC75310
0.8742	High Similarity	NPC469336
0.8734	High Similarity	NPC268905
0.8727	High Similarity	NPC302392
0.8727	High Similarity	NPC118086
0.8727	High Similarity	NPC470995
0.8726	High Similarity	NPC476122
0.872	High Similarity	NPC472651
0.8712	High Similarity	NPC261184
0.8712	High Similarity	NPC476858
0.8712	High Similarity	NPC476857
0.8712	High Similarity	NPC271657
0.8712	High Similarity	NPC476856
0.8704	High Similarity	NPC470939
0.8704	High Similarity	NPC149896
0.8704	High Similarity	NPC5079
0.8704	High Similarity	NPC207978
0.8704	High Similarity	NPC18347
0.8696	High Similarity	NPC475226
0.8693	High Similarity	NPC263337
0.8688	High Similarity	NPC107646
0.8679	High Similarity	NPC178932
0.8679	High Similarity	NPC253201
0.8679	High Similarity	NPC302054
0.8667	High Similarity	NPC472652
0.865	High Similarity	NPC469846
0.865	High Similarity	NPC234660
0.865	High Similarity	NPC51568
0.865	High Similarity	NPC198047
0.8645	High Similarity	NPC5676
0.8642	High Similarity	NPC475381
0.8636	High Similarity	NPC476946
0.8636	High Similarity	NPC64568
0.8634	High Similarity	NPC187149
0.8634	High Similarity	NPC470118
0.8634	High Similarity	NPC286722
0.8616	High Similarity	NPC33938
0.8616	High Similarity	NPC472672
0.8616	High Similarity	NPC475777
0.8614	High Similarity	NPC82602
0.8608	High Similarity	NPC469335
0.8608	High Similarity	NPC159927
0.8608	High Similarity	NPC477404
0.8608	High Similarity	NPC196864
0.8606	High Similarity	NPC476861
0.8606	High Similarity	NPC476853
0.8606	High Similarity	NPC476850
0.8606	High Similarity	NPC310572
0.8605	High Similarity	NPC472663
0.8605	High Similarity	NPC472662
0.8598	High Similarity	NPC27541
0.8598	High Similarity	NPC472664
0.8598	High Similarity	NPC62692
0.8598	High Similarity	NPC476860
0.8598	High Similarity	NPC61967
0.8598	High Similarity	NPC123088
0.8598	High Similarity	NPC126984
0.859	High Similarity	NPC97904
0.8589	High Similarity	NPC211777
0.8581	High Similarity	NPC84479
0.8581	High Similarity	NPC476944
0.858	High Similarity	NPC475295
0.858	High Similarity	NPC294149
0.858	High Similarity	NPC478177
0.858	High Similarity	NPC123153
0.858	High Similarity	NPC473473
0.858	High Similarity	NPC84349
0.8571	High Similarity	NPC94763
0.8571	High Similarity	NPC209364
0.8571	High Similarity	NPC236004
0.8571	High Similarity	NPC121158
0.8571	High Similarity	NPC471437
0.8571	High Similarity	NPC126723
0.8571	High Similarity	NPC469576
0.8562	High Similarity	NPC98206
0.8562	High Similarity	NPC34421
0.8562	High Similarity	NPC237259
0.8554	High Similarity	NPC472765
0.8554	High Similarity	NPC472766
0.8545	High Similarity	NPC23387
0.8544	High Similarity	NPC472654
0.8544	High Similarity	NPC195325
0.8537	High Similarity	NPC92589
0.8537	High Similarity	NPC224394
0.8537	High Similarity	NPC165218
0.8537	High Similarity	NPC663

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 NPC88841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	845
0.2-0.3	1772
0.3-0.4	2507
0.4-0.5	2115
0.5-0.6	1084
0.6-0.7	387
0.7-0.8	141
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD8434	Phase 2
0.8509	High Similarity	NPD5761	Phase 2
0.8509	High Similarity	NPD5760	Phase 2
0.8193	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7075	Discontinued
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7952	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7819	Suspended
0.7907	Intermediate Similarity	NPD7473	Discontinued
0.7892	Intermediate Similarity	NPD6801	Discontinued
0.7886	Intermediate Similarity	NPD6764	Approved
0.7886	Intermediate Similarity	NPD6765	Approved
0.7879	Intermediate Similarity	NPD6599	Discontinued
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3749	Approved
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD920	Approved
0.7759	Intermediate Similarity	NPD3818	Discontinued
0.7738	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6232	Discontinued
0.7732	Intermediate Similarity	NPD8404	Phase 2
0.7725	Intermediate Similarity	NPD7411	Suspended
0.7719	Intermediate Similarity	NPD5494	Approved
0.7714	Intermediate Similarity	NPD5844	Phase 1
0.7711	Intermediate Similarity	NPD3226	Approved
0.7709	Intermediate Similarity	NPD6785	Approved
0.7709	Intermediate Similarity	NPD6784	Approved
0.7692	Intermediate Similarity	NPD3817	Phase 2
0.7692	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1934	Approved
0.7665	Intermediate Similarity	NPD4380	Phase 2
0.7647	Intermediate Similarity	NPD3882	Suspended
0.7622	Intermediate Similarity	NPD6799	Approved
0.7602	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5402	Approved
0.7578	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2533	Approved
0.7576	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD6959	Discontinued
0.7572	Intermediate Similarity	NPD8127	Discontinued
0.7558	Intermediate Similarity	NPD6234	Discontinued
0.7558	Intermediate Similarity	NPD919	Approved
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD4967	Phase 2
0.7544	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7485	Intermediate Similarity	NPD2800	Approved
0.7485	Intermediate Similarity	NPD5403	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7472	Intermediate Similarity	NPD7074	Phase 3
0.747	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7768	Phase 2
0.743	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD1465	Phase 2
0.7425	Intermediate Similarity	NPD6273	Approved
0.7423	Intermediate Similarity	NPD1549	Phase 2
0.7416	Intermediate Similarity	NPD7054	Approved
0.7416	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1551	Phase 2
0.7407	Intermediate Similarity	NPD2796	Approved
0.7407	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6100	Approved
0.7391	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7472	Approved
0.7371	Intermediate Similarity	NPD7199	Phase 2
0.7371	Intermediate Similarity	NPD1247	Approved
0.7365	Intermediate Similarity	NPD5401	Approved
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3751	Discontinued
0.736	Intermediate Similarity	NPD7228	Approved
0.7348	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD3750	Approved
0.7317	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1511	Approved
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7251	Discontinued
0.7292	Intermediate Similarity	NPD7435	Discontinued
0.7288	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD1243	Approved
0.7268	Intermediate Similarity	NPD8407	Phase 2
0.7263	Intermediate Similarity	NPD7799	Discontinued
0.7256	Intermediate Similarity	NPD1471	Phase 3
0.7256	Intermediate Similarity	NPD2344	Approved
0.7253	Intermediate Similarity	NPD7808	Phase 3
0.7246	Intermediate Similarity	NPD7236	Approved
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7239	Intermediate Similarity	NPD1510	Phase 2
0.7238	Intermediate Similarity	NPD6797	Phase 2
0.7232	Intermediate Similarity	NPD3787	Discontinued
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD1512	Approved
0.7202	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8368	Discontinued
0.7198	Intermediate Similarity	NPD7685	Pre-registration
0.7195	Intermediate Similarity	NPD2935	Discontinued
0.7188	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD3764	Approved
0.7186	Intermediate Similarity	NPD6190	Approved
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7167	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD447	Suspended
0.716	Intermediate Similarity	NPD6355	Discontinued
0.7135	Intermediate Similarity	NPD6780	Approved
0.7135	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6779	Approved
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6782	Approved
0.7135	Intermediate Similarity	NPD6778	Approved
0.7135	Intermediate Similarity	NPD7239	Suspended
0.7135	Intermediate Similarity	NPD6776	Approved
0.7134	Intermediate Similarity	NPD3748	Approved
0.7127	Intermediate Similarity	NPD7286	Phase 2
0.7126	Intermediate Similarity	NPD7003	Approved
0.7126	Intermediate Similarity	NPD8166	Discontinued
0.7117	Intermediate Similarity	NPD1607	Approved
0.7117	Intermediate Similarity	NPD6651	Approved
0.7113	Intermediate Similarity	NPD7497	Discontinued
0.7112	Intermediate Similarity	NPD8361	Approved
0.7112	Intermediate Similarity	NPD8360	Approved
0.7104	Intermediate Similarity	NPD7240	Approved
0.7099	Intermediate Similarity	NPD1240	Approved
0.7083	Intermediate Similarity	NPD2309	Approved
0.7081	Intermediate Similarity	NPD3268	Approved
0.7073	Intermediate Similarity	NPD7097	Phase 1
0.7071	Intermediate Similarity	NPD7874	Approved
0.7071	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7907	Approved
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7049	Intermediate Similarity	NPD5953	Discontinued
0.7039	Intermediate Similarity	NPD5711	Approved
0.7039	Intermediate Similarity	NPD5710	Approved
0.7037	Intermediate Similarity	NPD8032	Phase 2
0.703	Intermediate Similarity	NPD4308	Phase 3
0.7029	Intermediate Similarity	NPD8455	Phase 2
0.7026	Intermediate Similarity	NPD7698	Approved
0.7026	Intermediate Similarity	NPD7697	Approved
0.7026	Intermediate Similarity	NPD7696	Phase 3
0.7024	Intermediate Similarity	NPD4110	Phase 3
0.7024	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8435	Approved
0.702	Intermediate Similarity	NPD8151	Discontinued
0.7019	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7095	Approved
0.7006	Intermediate Similarity	NPD1608	Approved
0.699	Remote Similarity	NPD7870	Phase 2
0.699	Remote Similarity	NPD8320	Phase 1
0.699	Remote Similarity	NPD8319	Approved
0.699	Remote Similarity	NPD7871	Phase 2
0.6981	Remote Similarity	NPD2797	Approved
0.6979	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6798	Discontinued
0.6975	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6823	Phase 2
0.697	Remote Similarity	NPD7701	Phase 2
0.6961	Remote Similarity	NPD4111	Phase 1
0.6961	Remote Similarity	NPD4665	Approved
0.695	Remote Similarity	NPD7783	Phase 2
0.695	Remote Similarity	NPD7801	Approved
0.695	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6005	Phase 3
0.6946	Remote Similarity	NPD6004	Phase 3
0.6946	Remote Similarity	NPD5762	Approved
0.6946	Remote Similarity	NPD5763	Approved
0.6946	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6002	Phase 3
0.6937	Remote Similarity	NPD5647	Approved
0.6933	Remote Similarity	NPD6233	Phase 2
0.6931	Remote Similarity	NPD4287	Approved
0.6919	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD8285	Discontinued
0.6899	Remote Similarity	NPD9717	Approved
0.6891	Remote Similarity	NPD8485	Approved
0.689	Remote Similarity	NPD4140	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