NPASS Compound

Structure

NPC470182 OpenBabel07101719132D 39 44 0 0 1 0 0 0 0 0999 V2000 -1.6638 2.8817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9913 0.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7644 1.6714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0165 -0.8935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2432 5.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3276 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9236 0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1594 0.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8632 0.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3276 2.8817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7235 2.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6638 1.9212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7008 1.8316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8319 0.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8319 3.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8232 1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4957 1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4957 0.4803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3276 1.9212 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7629 1.3214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2432 3.8170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1594 3.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9913 1.9212 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.9212 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1594 1.4409 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8319 1.4409 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6638 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8319 1.4409 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8319 0.4803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8319 4.3226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2826 3.8170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1594 4.3226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8319 2.4015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7175 -0.6556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7235 4.6489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3435 1.1177 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 -0.0000 2.8817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9913 2.8817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 4 27 1 0 0 0 0 5 35 1 0 0 0 0 6 8 1 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 25 1 0 0 0 0 9 36 1 0 0 0 0 10 19 1 0 0 0 0 10 22 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 17 2 0 0 0 0 12 28 1 0 0 0 0 13 16 2 0 0 0 0 13 36 1 0 0 0 0 14 26 1 0 0 0 0 14 37 1 0 0 0 0 15 30 2 0 0 0 0 15 38 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 27 1 6 0 0 0 19 25 1 6 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 32 2 0 0 0 0 22 39 1 0 0 0 0 23 25 1 1 0 0 0 23 39 1 0 0 0 0 24 26 1 6 0 0 0 24 28 1 0 0 0 0 24 38 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 27 29 1 1 0 0 0 28 29 1 1 0 0 0 28 33 1 0 0 0 0 29 34 1 1 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.23
Volume:	530.885
LogP:	2.733
LogD:	1.746
LogS:	-4.57
# Rotatable Bonds:	6
TPSA:	141.73
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	6.594
Fsp3:	0.69
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:	-5.292
MDCK Permeability:	6.703432882204652e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.764
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.868
Plasma Protein Binding (PPB):	69.58710479736328%
Volume Distribution (VD):	0.658
Pgp-substrate:	28.121986389160156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.362

ADMET: Excretion

Clearance (CL):	1.772
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.629
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.97
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.267
Carcinogencity:	0.92
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC470182

Natural Product ID:	NPC470182
*Common Name:**	Thaimoluccensin B
IUPAC Name:	n.a.
Synonyms:	Thaimoluccensin B
Standard InCHIKey:	YAHGGOMMTCUKNA-FDWGUHTBSA-N
Standard InCHI:	InChI=1S/C29H36O10/c1-15(30)38-24-26(3)14-37-29(34)27(4,20(26)11-21(31)35-5)18-6-8-25(2)19(17(18)12-28(24,29)33)10-22(32)39-23(25)16-7-9-36-13-16/h7,9,12-13,18-20,23-24,33-34H,6,8,10-11,14H2,1-5H3/t18-,19-,20-,23-,24-,25+,26-,27+,28+,29-/m0/s1
SMILES:	CC(=O)OC1C2(COC3(C1(C=C4C(C3(C2CC(=O)OC)C)CCC5(C4CC(=O)OC5C6=COC=C6)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1808139
PubChem CID:	56680328
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	27000.0	nM	PMID[559566]

☑ 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 NPC470182 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	378
0.1-0.2	1521
0.2-0.3	3336
0.3-0.4	5761
0.4-0.5	9764
0.5-0.6	9436
0.6-0.7	9489
0.7-0.8	2682
0.8-0.85	201
0.85-0.9	99
0.9-0.95	29
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9613	High Similarity	NPC200782
0.9487	High Similarity	NPC82851
0.9477	High Similarity	NPC282445
0.943	High Similarity	NPC97574
0.943	High Similarity	NPC93172
0.9427	High Similarity	NPC198047
0.9412	High Similarity	NPC476201
0.9367	High Similarity	NPC470940
0.9363	High Similarity	NPC211777
0.9304	High Similarity	NPC292389
0.9304	High Similarity	NPC469338
0.9295	High Similarity	NPC249021
0.929	High Similarity	NPC476262
0.9286	High Similarity	NPC469503
0.9255	High Similarity	NPC82602
0.925	High Similarity	NPC173516
0.9245	High Similarity	NPC469849
0.9245	High Similarity	NPC276551
0.9241	High Similarity	NPC207978
0.9241	High Similarity	NPC149896
0.9236	High Similarity	NPC307383
0.9226	High Similarity	NPC30222
0.9198	High Similarity	NPC160818
0.9198	High Similarity	NPC169299
0.9193	High Similarity	NPC471397
0.9187	High Similarity	NPC470875
0.9187	High Similarity	NPC472141
0.9182	High Similarity	NPC472139
0.9182	High Similarity	NPC477405
0.9182	High Similarity	NPC472773
0.9172	High Similarity	NPC299038
0.9172	High Similarity	NPC261597
0.9172	High Similarity	NPC36655
0.9167	High Similarity	NPC264943
0.9167	High Similarity	NPC35000
0.9156	High Similarity	NPC476122
0.9146	High Similarity	NPC262386
0.913	High Similarity	NPC100333
0.9125	High Similarity	NPC271657
0.9119	High Similarity	NPC472771
0.9119	High Similarity	NPC69028
0.9119	High Similarity	NPC18347
0.9114	High Similarity	NPC262872
0.9114	High Similarity	NPC475967
0.9074	High Similarity	NPC160651
0.9074	High Similarity	NPC271235
0.9062	High Similarity	NPC302369
0.9062	High Similarity	NPC134254
0.9062	High Similarity	NPC288602
0.9062	High Similarity	NPC39986
0.9062	High Similarity	NPC88841
0.9057	High Similarity	NPC477402
0.9057	High Similarity	NPC472653
0.9051	High Similarity	NPC472776
0.9051	High Similarity	NPC472778
0.9051	High Similarity	NPC45101
0.9051	High Similarity	NPC472777
0.9045	High Similarity	NPC44675
0.9045	High Similarity	NPC214541
0.9045	High Similarity	NPC469336
0.9038	High Similarity	NPC44577
0.9012	High Similarity	NPC472775
0.9012	High Similarity	NPC472774
0.9	High Similarity	NPC329938
0.9	High Similarity	NPC5079
0.9	High Similarity	NPC188649
0.8994	High Similarity	NPC477403
0.8981	High Similarity	NPC178932
0.8968	High Similarity	NPC69647
0.8968	High Similarity	NPC125182
0.8961	High Similarity	NPC255414
0.8957	High Similarity	NPC296558
0.8944	High Similarity	NPC419
0.8944	High Similarity	NPC51568
0.8944	High Similarity	NPC234660
0.8938	High Similarity	NPC335761
0.8931	High Similarity	NPC286722
0.8931	High Similarity	NPC167142
0.8931	High Similarity	NPC472772
0.8931	High Similarity	NPC187149
0.891	High Similarity	NPC196864
0.891	High Similarity	NPC159927
0.891	High Similarity	NPC469335
0.891	High Similarity	NPC477404
0.8896	High Similarity	NPC472282
0.8896	High Similarity	NPC472651
0.8889	High Similarity	NPC146991
0.8882	High Similarity	NPC193798
0.8882	High Similarity	NPC263432
0.8875	High Similarity	NPC475295
0.8875	High Similarity	NPC473473
0.8868	High Similarity	NPC469485
0.8868	High Similarity	NPC209364
0.8854	High Similarity	NPC18135
0.8841	High Similarity	NPC472652
0.8839	High Similarity	NPC470941
0.8827	High Similarity	NPC469846
0.8827	High Similarity	NPC476197
0.882	High Similarity	NPC25255
0.8812	High Similarity	NPC173544
0.8812	High Similarity	NPC88007
0.8812	High Similarity	NPC472283
0.8805	High Similarity	NPC469850
0.8797	High Similarity	NPC268905
0.8774	High Similarity	NPC346
0.8773	High Similarity	NPC476858
0.8773	High Similarity	NPC476856
0.8773	High Similarity	NPC476857
0.8766	High Similarity	NPC476944
0.8765	High Similarity	NPC290400
0.8765	High Similarity	NPC117986
0.8765	High Similarity	NPC96443
0.8765	High Similarity	NPC470792
0.8765	High Similarity	NPC68848
0.8765	High Similarity	NPC470939
0.8758	High Similarity	NPC475226
0.8757	High Similarity	NPC470938
0.875	High Similarity	NPC472665
0.875	High Similarity	NPC478177
0.875	High Similarity	NPC126723
0.875	High Similarity	NPC107646
0.8743	High Similarity	NPC94763
0.8743	High Similarity	NPC236004
0.8742	High Similarity	NPC57998
0.872	High Similarity	NPC121995
0.8718	High Similarity	NPC250228
0.8712	High Similarity	NPC165218
0.871	High Similarity	NPC5676
0.8704	High Similarity	NPC475381
0.8701	High Similarity	NPC476946
0.8696	High Similarity	NPC470118
0.8696	High Similarity	NPC194499
0.8696	High Similarity	NPC195954
0.8688	High Similarity	NPC281258
0.8679	High Similarity	NPC476939
0.8679	High Similarity	NPC33938
0.8679	High Similarity	NPC476940
0.8667	High Similarity	NPC476861
0.8667	High Similarity	NPC476850
0.8667	High Similarity	NPC476853
0.8659	High Similarity	NPC123088
0.8659	High Similarity	NPC476860
0.865	High Similarity	NPC18986
0.8642	High Similarity	NPC474611
0.8636	High Similarity	NPC121158
0.8634	High Similarity	NPC60973
0.8625	High Similarity	NPC302054
0.8625	High Similarity	NPC253201
0.8614	High Similarity	NPC472766
0.8614	High Similarity	NPC472765
0.8608	High Similarity	NPC472654
0.8608	High Similarity	NPC195325
0.8606	High Similarity	NPC23387
0.8606	High Similarity	NPC475779
0.8599	High Similarity	NPC221809
0.8598	High Similarity	NPC285567
0.8598	High Similarity	NPC663
0.8598	High Similarity	NPC224394
0.859	High Similarity	NPC41182
0.8589	High Similarity	NPC287559
0.8589	High Similarity	NPC8389
0.8589	High Similarity	NPC305016
0.8589	High Similarity	NPC470789
0.8571	High Similarity	NPC155939
0.8571	High Similarity	NPC296807
0.8571	High Similarity	NPC141538
0.8571	High Similarity	NPC92979
0.8563	High Similarity	NPC470995
0.8562	High Similarity	NPC472672
0.8562	High Similarity	NPC147168
0.8554	High Similarity	NPC270312
0.8554	High Similarity	NPC472764
0.8554	High Similarity	NPC473753
0.8554	High Similarity	NPC473766
0.8553	High Similarity	NPC470997
0.8537	High Similarity	NPC79571
0.8528	High Similarity	NPC237155
0.8528	High Similarity	NPC472671
0.8526	High Similarity	NPC251865
0.8526	High Similarity	NPC137295
0.8521	High Similarity	NPC471437
0.8521	High Similarity	NPC469576
0.8521	High Similarity	NPC477824
0.8519	High Similarity	NPC41880
0.8512	High Similarity	NPC294512
0.8512	High Similarity	NPC159232
0.8509	High Similarity	NPC34421
0.8509	High Similarity	NPC237259
0.8509	High Similarity	NPC98206
0.8503	High Similarity	NPC327922
0.8497	Intermediate Similarity	NPC242068
0.8497	Intermediate Similarity	NPC247563
0.8494	Intermediate Similarity	NPC478178
0.8494	Intermediate Similarity	NPC472670
0.8494	Intermediate Similarity	NPC307781
0.8494	Intermediate Similarity	NPC277618
0.8491	Intermediate Similarity	NPC211625
0.8491	Intermediate Similarity	NPC470998
0.8491	Intermediate Similarity	NPC234494
0.8485	Intermediate Similarity	NPC283209

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 NPC470182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	1064
0.2-0.3	2229
0.3-0.4	2641
0.4-0.5	1882
0.5-0.6	715
0.6-0.7	261
0.7-0.8	32
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
0.8457	Intermediate Similarity	NPD5760	Phase 2
0.8457	Intermediate Similarity	NPD5761	Phase 2
0.8439	Intermediate Similarity	NPD8434	Phase 2
0.774	Intermediate Similarity	NPD6559	Discontinued
0.7719	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7075	Discontinued
0.7556	Intermediate Similarity	NPD8312	Approved
0.7556	Intermediate Similarity	NPD8313	Approved
0.7554	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7074	Phase 3
0.7513	Intermediate Similarity	NPD8404	Phase 2
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7054	Approved
0.7472	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5494	Approved
0.7457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6764	Approved
0.7444	Intermediate Similarity	NPD6765	Approved
0.743	Intermediate Similarity	NPD7472	Approved
0.7416	Intermediate Similarity	NPD7228	Approved
0.7416	Intermediate Similarity	NPD3818	Discontinued
0.7374	Intermediate Similarity	NPD5844	Phase 1
0.7356	Intermediate Similarity	NPD3749	Approved
0.7348	Intermediate Similarity	NPD7251	Discontinued
0.7318	Intermediate Similarity	NPD3751	Discontinued
0.731	Intermediate Similarity	NPD6599	Discontinued
0.731	Intermediate Similarity	NPD4380	Phase 2
0.7308	Intermediate Similarity	NPD7808	Phase 3
0.7303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6166	Phase 2
0.7303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6797	Phase 2
0.7289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6784	Approved
0.7283	Intermediate Similarity	NPD6785	Approved
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7263	Intermediate Similarity	NPD7473	Discontinued
0.7258	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7243	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6959	Discontinued
0.7225	Intermediate Similarity	NPD37	Approved
0.7225	Intermediate Similarity	NPD6801	Discontinued
0.7225	Intermediate Similarity	NPD1934	Approved
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6234	Discontinued
0.7213	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4966	Approved
0.72	Intermediate Similarity	NPD4965	Approved
0.72	Intermediate Similarity	NPD4967	Phase 2
0.7198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6232	Discontinued
0.7184	Intermediate Similarity	NPD1465	Phase 2
0.7165	Intermediate Similarity	NPD7435	Discontinued
0.7158	Intermediate Similarity	NPD7685	Pre-registration
0.7158	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD5402	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD920	Approved
0.7118	Intermediate Similarity	NPD2532	Approved
0.7118	Intermediate Similarity	NPD2533	Approved
0.7118	Intermediate Similarity	NPD2534	Approved
0.7111	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD8455	Phase 2
0.7059	Intermediate Similarity	NPD6799	Approved
0.7052	Intermediate Similarity	NPD3226	Approved
0.7043	Intermediate Similarity	NPD8407	Phase 2
0.7039	Intermediate Similarity	NPD7199	Phase 2
0.7039	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5403	Approved
0.7033	Intermediate Similarity	NPD7799	Discontinued
0.703	Intermediate Similarity	NPD7097	Phase 1
0.7022	Intermediate Similarity	NPD919	Approved
0.7018	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6779	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD6778	Approved
0.701	Intermediate Similarity	NPD6780	Approved
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7697	Approved
0.699	Remote Similarity	NPD7698	Approved
0.699	Remote Similarity	NPD7696	Phase 3
0.6989	Remote Similarity	NPD2801	Approved
0.6985	Remote Similarity	NPD8151	Discontinued
0.6982	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD6273	Approved
0.6973	Remote Similarity	NPD8368	Discontinued
0.6964	Remote Similarity	NPD1549	Phase 2
0.6961	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8320	Phase 1
0.6954	Remote Similarity	NPD8319	Approved
0.6954	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7874	Approved
0.695	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6099	Approved
0.6946	Remote Similarity	NPD6100	Approved
0.6946	Remote Similarity	NPD1551	Phase 2
0.6936	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7701	Phase 2
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2800	Approved
0.6919	Remote Similarity	NPD5401	Approved
0.6919	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2346	Discontinued
0.6904	Remote Similarity	NPD7497	Discontinued
0.6901	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8360	Approved
0.6895	Remote Similarity	NPD8361	Approved
0.6869	Remote Similarity	NPD7871	Phase 2
0.6869	Remote Similarity	NPD7870	Phase 2
0.6864	Remote Similarity	NPD970	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7907	Approved
0.686	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6823	Phase 2
0.6851	Remote Similarity	NPD1247	Approved
0.6845	Remote Similarity	NPD2796	Approved
0.6832	Remote Similarity	NPD7801	Approved
0.6821	Remote Similarity	NPD7699	Phase 2
0.6821	Remote Similarity	NPD7700	Phase 2
0.6811	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8435	Approved
0.6802	Remote Similarity	NPD7236	Approved
0.6786	Remote Similarity	NPD3748	Approved
0.6786	Remote Similarity	NPD2799	Discontinued
0.6786	Remote Similarity	NPD7033	Discontinued
0.6784	Remote Similarity	NPD8166	Discontinued
0.6784	Remote Similarity	NPD7003	Approved
0.6776	Remote Similarity	NPD3926	Phase 2
0.6763	Remote Similarity	NPD4665	Approved
0.6763	Remote Similarity	NPD4111	Phase 1
0.6763	Remote Similarity	NPD1511	Approved
0.6753	Remote Similarity	NPD6534	Approved
0.6753	Remote Similarity	NPD6535	Approved
0.6746	Remote Similarity	NPD2935	Discontinued
0.6734	Remote Similarity	NPD7680	Approved
0.6727	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1243	Approved
0.6721	Remote Similarity	NPD5711	Approved
0.6721	Remote Similarity	NPD7229	Phase 3
0.6721	Remote Similarity	NPD5710	Approved
0.6707	Remote Similarity	NPD6355	Discontinued
0.6707	Remote Similarity	NPD1933	Approved
0.6707	Remote Similarity	NPD6832	Phase 2
0.6707	Remote Similarity	NPD447	Suspended
0.6706	Remote Similarity	NPD2344	Approved
0.6706	Remote Similarity	NPD1471	Phase 3
0.6705	Remote Similarity	NPD7239	Suspended
0.6701	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1510	Phase 2
0.6686	Remote Similarity	NPD1512	Approved
0.6686	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6190	Approved
0.6629	Remote Similarity	NPD7028	Phase 2
0.6627	Remote Similarity	NPD3764	Approved
0.6627	Remote Similarity	NPD2313	Discontinued
0.6619	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD8285	Discontinued
0.6615	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7266	Discontinued
0.6607	Remote Similarity	NPD230	Phase 1
0.66	Remote Similarity	NPD3057	Approved
0.6599	Remote Similarity	NPD8485	Approved
0.6592	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4110	Phase 3
0.6588	Remote Similarity	NPD4308	Phase 3
0.6583	Remote Similarity	NPD4107	Approved
0.657	Remote Similarity	NPD7930	Approved
0.6568	Remote Similarity	NPD1607	Approved
0.6568	Remote Similarity	NPD6651	Approved
0.6561	Remote Similarity	NPD5953	Discontinued
0.6552	Remote Similarity	NPD7583	Approved
0.6552	Remote Similarity	NPD7584	Approved
0.6552	Remote Similarity	NPD2309	Approved
0.6548	Remote Similarity	NPD1240	Approved
0.6546	Remote Similarity	NPD4287	Approved
0.6543	Remote Similarity	NPD1608	Approved
0.6543	Remote Similarity	NPD7286	Phase 2

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