NPASS Compound

Structure

NPC8389 OpenBabel07101719512D 37 41 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 2.5981 1.5000 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 -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 -2.5981 1.5000 0.0000 C 0 0 1 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 4.3301 1.5000 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 1.7321 1.0000 0.0000 C 0 0 0 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 2 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 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -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 2 20 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 35 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 1 1 6 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 32 2 0 0 0 0 20 36 1 0 0 0 0 22 24 2 0 0 0 0 23 26 1 0 0 0 0 23 30 1 1 0 0 0 24 35 1 0 0 0 0 25 33 2 0 0 0 0 25 37 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 0 0 0 0 28 31 1 0 0 0 0 28 37 1 0 0 0 0 29 31 1 0 0 0 0 30 31 1 0 0 0 0 31 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.27
Volume:	533.599
LogP:	5.068
LogD:	4.536
LogS:	-5.286
# Rotatable Bonds:	6
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	4.771
Fsp3:	0.548
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:	-4.843
MDCK Permeability:	2.076932469208259e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	99.32661437988281%
Volume Distribution (VD):	2.66
Pgp-substrate:	3.558098793029785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.571
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.813
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.3
CYP2D6-inhibitor:	0.841
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	4.907
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.628
Human Hepatotoxicity (H-HT):	0.59
Drug-inuced Liver Injury (DILI):	0.923
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.76
Carcinogencity:	0.142
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC8389

Natural Product ID:	NPC8389
*Common Name:**	6Beta-Cinnamoyloxy-7Beta-Acetoxyvouacapen-5Alpha-Ol
IUPAC Name:	[(4aR,5R,6R,6aS,7R,11aS,11bR)-6-acetyloxy-4a-hydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-5-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	NQXXHQFQXKHFLH-JLTDNTAYSA-N
Standard InCHI:	InChI=1S/C31H38O6/c1-19-22-14-17-35-24(22)18-23-26(19)27(36-20(2)32)28(31(34)29(3,4)15-9-16-30(23,31)5)37-25(33)13-12-21-10-7-6-8-11-21/h6-8,10-14,17,19,23,26-28,34H,9,15-16,18H2,1-5H3/b13-12+/t19-,23-,26-,27+,28+,30+,31+/m0/s1
SMILES:	C[C@H]1c2ccoc2C[C@H]2[C@H]1[C@H]([C@H]([C@]1(C(C)(C)CCC[C@]21C)O)OC(=O)/C=C/c1ccccc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097166
PubChem CID:	46861633
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
NPO32590	caesalpinia sp.	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356735]

☑ 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
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	33410.0	nM	PMID[504784]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	17370.0	nM	PMID[504784]

☑ 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 NPC8389 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	340
0.1-0.2	1277
0.2-0.3	2587
0.3-0.4	4947
0.4-0.5	9830
0.5-0.6	8499
0.6-0.7	6518
0.7-0.8	7934
0.8-0.85	554
0.85-0.9	169
0.9-0.95	35
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC79571
0.9867	High Similarity	NPC7059
0.974	High Similarity	NPC277618
0.9615	High Similarity	NPC296558
0.9605	High Similarity	NPC194499
0.9605	High Similarity	NPC88007
0.9477	High Similarity	NPC195954
0.947	High Similarity	NPC121615
0.947	High Similarity	NPC294511
0.9467	High Similarity	NPC228842
0.9467	High Similarity	NPC212257
0.9419	High Similarity	NPC68848
0.9295	High Similarity	NPC18986
0.9295	High Similarity	NPC188649
0.9267	High Similarity	NPC71821
0.9236	High Similarity	NPC88841
0.9236	High Similarity	NPC285567
0.9236	High Similarity	NPC283209
0.9236	High Similarity	NPC288602
0.9182	High Similarity	NPC310572
0.9182	High Similarity	NPC41689
0.9167	High Similarity	NPC474611
0.9161	High Similarity	NPC41880
0.9119	High Similarity	NPC121995
0.9108	High Similarity	NPC287559
0.9038	High Similarity	NPC104736
0.902	High Similarity	NPC69647
0.902	High Similarity	NPC125182
0.9013	High Similarity	NPC255414
0.9006	High Similarity	NPC255787
0.9006	High Similarity	NPC291742
0.9	High Similarity	NPC308156
0.8994	High Similarity	NPC14499
0.8994	High Similarity	NPC475039
0.8994	High Similarity	NPC476035
0.8981	High Similarity	NPC304692
0.8963	High Similarity	NPC56953
0.8963	High Similarity	NPC176413
0.8951	High Similarity	NPC118086
0.8944	High Similarity	NPC270312
0.8938	High Similarity	NPC56358
0.8933	High Similarity	NPC263337
0.8931	High Similarity	NPC471003
0.8924	High Similarity	NPC123153
0.8896	High Similarity	NPC294512
0.8896	High Similarity	NPC475641
0.8896	High Similarity	NPC475237
0.8861	High Similarity	NPC81405
0.882	High Similarity	NPC61967
0.882	High Similarity	NPC62692
0.882	High Similarity	NPC126984
0.882	High Similarity	NPC27541
0.8805	High Similarity	NPC140952
0.8774	High Similarity	NPC211625
0.8765	High Similarity	NPC86800
0.8758	High Similarity	NPC5676
0.8743	High Similarity	NPC11062
0.8733	High Similarity	NPC202260
0.8726	High Similarity	NPC268905
0.872	High Similarity	NPC88593
0.872	High Similarity	NPC302392
0.8704	High Similarity	NPC276735
0.8696	High Similarity	NPC82851
0.8696	High Similarity	NPC200782
0.8688	High Similarity	NPC84349
0.8684	High Similarity	NPC121158
0.8671	High Similarity	NPC253201
0.8671	High Similarity	NPC302054
0.8671	High Similarity	NPC98206
0.8671	High Similarity	NPC34421
0.8671	High Similarity	NPC237259
0.8659	High Similarity	NPC160651
0.865	High Similarity	NPC475779
0.8645	High Similarity	NPC286038
0.8645	High Similarity	NPC216755
0.8642	High Similarity	NPC469338
0.8642	High Similarity	NPC472773
0.8642	High Similarity	NPC292389
0.8634	High Similarity	NPC472299
0.8625	High Similarity	NPC299038
0.8616	High Similarity	NPC155939
0.8616	High Similarity	NPC296807
0.8616	High Similarity	NPC141538
0.8608	High Similarity	NPC48671
0.8608	High Similarity	NPC246164
0.8608	High Similarity	NPC472672
0.8608	High Similarity	NPC476201
0.86	High Similarity	NPC307401
0.8598	High Similarity	NPC173516
0.859	High Similarity	NPC66991
0.8589	High Similarity	NPC469849
0.8589	High Similarity	NPC276551
0.8589	High Similarity	NPC470182
0.8589	High Similarity	NPC470940
0.858	High Similarity	NPC470792
0.858	High Similarity	NPC472771
0.8571	High Similarity	NPC475967
0.8571	High Similarity	NPC472665
0.8553	High Similarity	NPC114880
0.8553	High Similarity	NPC282445
0.8545	High Similarity	NPC271235
0.8545	High Similarity	NPC471397
0.8537	High Similarity	NPC470875
0.8535	High Similarity	NPC234494
0.8528	High Similarity	NPC302369
0.8528	High Similarity	NPC134254
0.8528	High Similarity	NPC39986
0.8528	High Similarity	NPC477405
0.8526	High Similarity	NPC471174
0.8519	High Similarity	NPC335761
0.8509	High Similarity	NPC249021
0.8509	High Similarity	NPC472776
0.8509	High Similarity	NPC472777
0.8509	High Similarity	NPC472778
0.8506	High Similarity	NPC241951
0.8506	High Similarity	NPC57628
0.8506	High Similarity	NPC470152
0.8506	High Similarity	NPC188865
0.8506	High Similarity	NPC95265
0.8506	High Similarity	NPC472570
0.8506	High Similarity	NPC475122
0.8506	High Similarity	NPC472573
0.8506	High Similarity	NPC11685
0.8506	High Similarity	NPC95810
0.8506	High Similarity	NPC475759
0.8506	High Similarity	NPC243577
0.8506	High Similarity	NPC472569
0.8506	High Similarity	NPC70716
0.8506	High Similarity	NPC125106
0.8506	High Similarity	NPC25768
0.8506	High Similarity	NPC476974
0.8506	High Similarity	NPC163719
0.85	High Similarity	NPC25351
0.85	High Similarity	NPC264943
0.85	High Similarity	NPC92979
0.85	High Similarity	NPC476262
0.8494	Intermediate Similarity	NPC470995
0.8491	Intermediate Similarity	NPC33938
0.8491	Intermediate Similarity	NPC469503
0.8485	Intermediate Similarity	NPC472774
0.8485	Intermediate Similarity	NPC472282
0.8485	Intermediate Similarity	NPC472775
0.8485	Intermediate Similarity	NPC473766
0.8485	Intermediate Similarity	NPC473753
0.8481	Intermediate Similarity	NPC470997
0.8471	Intermediate Similarity	NPC19747
0.8466	Intermediate Similarity	NPC18347
0.8466	Intermediate Similarity	NPC149896
0.8466	Intermediate Similarity	NPC329938
0.8466	Intermediate Similarity	NPC5079
0.8466	Intermediate Similarity	NPC69028
0.8466	Intermediate Similarity	NPC263432
0.8462	Intermediate Similarity	NPC62799
0.8457	Intermediate Similarity	NPC307383
0.8457	Intermediate Similarity	NPC472671
0.8452	Intermediate Similarity	NPC470159
0.8452	Intermediate Similarity	NPC174982
0.8452	Intermediate Similarity	NPC158663
0.8452	Intermediate Similarity	NPC171525
0.8452	Intermediate Similarity	NPC476973
0.8452	Intermediate Similarity	NPC177940
0.8452	Intermediate Similarity	NPC469349
0.8452	Intermediate Similarity	NPC148185
0.8452	Intermediate Similarity	NPC251865
0.8452	Intermediate Similarity	NPC29704
0.8452	Intermediate Similarity	NPC471104
0.8452	Intermediate Similarity	NPC70403
0.8452	Intermediate Similarity	NPC184817
0.8452	Intermediate Similarity	NPC472568
0.8452	Intermediate Similarity	NPC473088
0.8452	Intermediate Similarity	NPC472571
0.8452	Intermediate Similarity	NPC200471
0.8452	Intermediate Similarity	NPC472572
0.8452	Intermediate Similarity	NPC96903
0.8452	Intermediate Similarity	NPC472575
0.8452	Intermediate Similarity	NPC470157
0.8447	Intermediate Similarity	NPC107646
0.8442	Intermediate Similarity	NPC163087
0.8438	Intermediate Similarity	NPC30222
0.8438	Intermediate Similarity	NPC178932
0.8431	Intermediate Similarity	NPC148374
0.8431	Intermediate Similarity	NPC224491
0.8431	Intermediate Similarity	NPC67003
0.8428	Intermediate Similarity	NPC119252
0.8424	Intermediate Similarity	NPC97574
0.8424	Intermediate Similarity	NPC93172
0.8424	Intermediate Similarity	NPC472141
0.8418	Intermediate Similarity	NPC471001
0.8415	Intermediate Similarity	NPC51568
0.8415	Intermediate Similarity	NPC234660
0.8415	Intermediate Similarity	NPC469889
0.8415	Intermediate Similarity	NPC476197
0.8408	Intermediate Similarity	NPC473215
0.8405	Intermediate Similarity	NPC472653
0.8397	Intermediate Similarity	NPC41182
0.8395	Intermediate Similarity	NPC472772
0.8395	Intermediate Similarity	NPC475066
0.8395	Intermediate Similarity	NPC470119
0.8395	Intermediate Similarity	NPC470118
0.8395	Intermediate Similarity	NPC214495

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 NPC8389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	799
0.2-0.3	1459
0.3-0.4	2493
0.4-0.5	2208
0.5-0.6	1255
0.6-0.7	482
0.7-0.8	158
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8698	High Similarity	NPD8434	Phase 2
0.8323	Intermediate Similarity	NPD4628	Phase 3
0.8063	Intermediate Similarity	NPD6273	Approved
0.8049	Intermediate Similarity	NPD5760	Phase 2
0.8049	Intermediate Similarity	NPD5761	Phase 2
0.8049	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7458	Discontinued
0.7977	Intermediate Similarity	NPD6764	Approved
0.7977	Intermediate Similarity	NPD6765	Approved
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7939	Intermediate Similarity	NPD7819	Suspended
0.7911	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD5844	Phase 1
0.7904	Intermediate Similarity	NPD7075	Discontinued
0.7898	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD8127	Discontinued
0.7844	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3749	Approved
0.7797	Intermediate Similarity	NPD6784	Approved
0.7797	Intermediate Similarity	NPD6785	Approved
0.7785	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7716	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD7411	Suspended
0.7706	Intermediate Similarity	NPD5494	Approved
0.7679	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6801	Discontinued
0.7647	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD919	Approved
0.764	Intermediate Similarity	NPD3750	Approved
0.764	Intermediate Similarity	NPD7003	Approved
0.764	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7768	Phase 2
0.7619	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.7584	Intermediate Similarity	NPD8312	Approved
0.7584	Intermediate Similarity	NPD8313	Approved
0.7582	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6355	Discontinued
0.7576	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD920	Approved
0.7574	Intermediate Similarity	NPD3817	Phase 2
0.756	Intermediate Similarity	NPD1934	Approved
0.7558	Intermediate Similarity	NPD7199	Phase 2
0.7547	Intermediate Similarity	NPD3748	Approved
0.7546	Intermediate Similarity	NPD7236	Approved
0.7546	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4380	Phase 2
0.7538	Intermediate Similarity	NPD8404	Phase 2
0.7531	Intermediate Similarity	NPD8166	Discontinued
0.7529	Intermediate Similarity	NPD3882	Suspended
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3226	Approved
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5403	Approved
0.746	Intermediate Similarity	NPD7497	Discontinued
0.7457	Intermediate Similarity	NPD6959	Discontinued
0.7456	Intermediate Similarity	NPD37	Approved
0.7455	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5401	Approved
0.7443	Intermediate Similarity	NPD3818	Discontinued
0.7442	Intermediate Similarity	NPD6234	Discontinued
0.7438	Intermediate Similarity	NPD2799	Discontinued
0.7436	Intermediate Similarity	NPD7095	Approved
0.7434	Intermediate Similarity	NPD1608	Approved
0.7429	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6166	Phase 2
0.7429	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4965	Approved
0.7427	Intermediate Similarity	NPD4966	Approved
0.7427	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD6232	Discontinued
0.7412	Intermediate Similarity	NPD8455	Phase 2
0.7407	Intermediate Similarity	NPD1549	Phase 2
0.7391	Intermediate Similarity	NPD1551	Phase 2
0.7389	Intermediate Similarity	NPD6798	Discontinued
0.7389	Intermediate Similarity	NPD3764	Approved
0.7377	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5402	Approved
0.7362	Intermediate Similarity	NPD1243	Approved
0.736	Intermediate Similarity	NPD7074	Phase 3
0.7349	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1471	Phase 3
0.7346	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2346	Discontinued
0.7345	Intermediate Similarity	NPD7177	Discontinued
0.7345	Intermediate Similarity	NPD7228	Approved
0.7342	Intermediate Similarity	NPD8032	Phase 2
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7325	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7239	Suspended
0.7317	Intermediate Similarity	NPD4110	Phase 3
0.7317	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7229	Phase 3
0.7314	Intermediate Similarity	NPD3787	Discontinued
0.731	Intermediate Similarity	NPD2801	Approved
0.731	Intermediate Similarity	NPD1465	Phase 2
0.7303	Intermediate Similarity	NPD7054	Approved
0.7303	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7685	Pre-registration
0.7278	Intermediate Similarity	NPD3268	Approved
0.7268	Intermediate Similarity	NPD8150	Discontinued
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7263	Intermediate Similarity	NPD7472	Approved
0.7257	Intermediate Similarity	NPD1247	Approved
0.7247	Intermediate Similarity	NPD7799	Discontinued
0.7247	Intermediate Similarity	NPD3751	Discontinued
0.7247	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2532	Approved
0.7246	Intermediate Similarity	NPD2533	Approved
0.7246	Intermediate Similarity	NPD2534	Approved
0.7239	Intermediate Similarity	NPD2344	Approved
0.7239	Intermediate Similarity	NPD5763	Approved
0.7239	Intermediate Similarity	NPD5762	Approved
0.7237	Intermediate Similarity	NPD17	Approved
0.7233	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD1510	Phase 2
0.7208	Intermediate Similarity	NPD3972	Approved
0.7195	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4140	Approved
0.7188	Intermediate Similarity	NPD7435	Discontinued
0.7186	Intermediate Similarity	NPD1511	Approved
0.7182	Intermediate Similarity	NPD7240	Approved
0.7182	Intermediate Similarity	NPD7251	Discontinued
0.7179	Intermediate Similarity	NPD2797	Approved
0.7175	Intermediate Similarity	NPD3926	Phase 2
0.717	Intermediate Similarity	NPD2313	Discontinued
0.7169	Intermediate Similarity	NPD3887	Approved
0.7169	Intermediate Similarity	NPD2354	Approved
0.7169	Intermediate Similarity	NPD6190	Approved
0.7168	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7028	Phase 2
0.7127	Intermediate Similarity	NPD6797	Phase 2
0.712	Intermediate Similarity	NPD4107	Approved
0.7101	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1512	Approved
0.7099	Intermediate Similarity	NPD1607	Approved
0.7093	Intermediate Similarity	NPD6677	Suspended
0.7081	Intermediate Similarity	NPD4307	Phase 2
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7081	Intermediate Similarity	NPD1240	Approved
0.7073	Intermediate Similarity	NPD2438	Suspended
0.7073	Intermediate Similarity	NPD2935	Discontinued
0.707	Intermediate Similarity	NPD3266	Approved
0.707	Intermediate Similarity	NPD3267	Approved
0.7066	Intermediate Similarity	NPD2309	Approved
0.7065	Intermediate Similarity	NPD8407	Phase 2
0.7048	Intermediate Similarity	NPD2800	Approved
0.7047	Intermediate Similarity	NPD3057	Approved
0.7041	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5735	Approved
0.7031	Intermediate Similarity	NPD6776	Approved
0.7031	Intermediate Similarity	NPD6780	Approved
0.7031	Intermediate Similarity	NPD6777	Approved
0.7031	Intermediate Similarity	NPD6779	Approved
0.7031	Intermediate Similarity	NPD6781	Approved
0.7031	Intermediate Similarity	NPD6778	Approved
0.7031	Intermediate Similarity	NPD6782	Approved
0.703	Intermediate Similarity	NPD6005	Phase 3
0.703	Intermediate Similarity	NPD6004	Phase 3
0.703	Intermediate Similarity	NPD6002	Phase 3
0.703	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2798	Approved
0.7013	Intermediate Similarity	NPD1778	Approved
0.7006	Intermediate Similarity	NPD1283	Approved
0.7005	Intermediate Similarity	NPD8435	Approved
0.7005	Intermediate Similarity	NPD8360	Approved
0.7005	Intermediate Similarity	NPD8361	Approved
0.7	Intermediate Similarity	NPD7008	Discontinued
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6995	Remote Similarity	NPD8368	Discontinued
0.6995	Remote Similarity	NPD4482	Phase 3
0.6989	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4534	Discontinued
0.697	Remote Similarity	NPD7874	Approved
0.697	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7047	Phase 3
0.6963	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2972	Approved
0.6959	Remote Similarity	NPD3533	Approved
0.6957	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7577	Discontinued
0.6937	Remote Similarity	NPD4908	Phase 1

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