NPASS Compound

Structure

NPC473602 OpenBabel07101719162D 50 55 0 0 1 0 0 0 0 0999 V2000 7.1587 2.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7847 -3.5131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2035 -0.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6906 0.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8898 0.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2663 -0.4970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2759 0.1557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5684 1.9992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6133 -1.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9055 1.5640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0471 1.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7789 1.0770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0620 0.0512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7939 0.0771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4914 2.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4874 2.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7399 -0.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8664 -0.0265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3152 1.0252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3601 -1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2853 3.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6432 -3.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9354 -0.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1235 1.4088 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0984 1.6313 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 2.1906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7099 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5983 -0.0006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3302 0.0253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2185 -1.4616 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4418 1.5122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4867 -1.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1235 1.4088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9504 -1.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2036 -0.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8515 0.9734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5833 0.9993 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4717 -0.4876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2703 4.0249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5166 -3.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9339 3.0916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0984 1.6313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8238 -1.9226 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 5.4268 2.5121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6282 -2.0004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0919 -1.9485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 37 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 38 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 2 0 0 0 0 17 18 1 0 0 0 0 17 30 1 0 0 0 0 18 39 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 31 1 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 21 34 1 0 0 0 0 22 26 1 0 0 0 0 22 47 1 0 0 0 0 23 42 2 0 0 0 0 23 48 1 0 0 0 0 24 43 2 0 0 0 0 24 49 1 0 0 0 0 25 36 1 0 0 0 0 26 27 1 0 0 0 0 27 39 1 6 0 0 0 28 35 1 0 0 0 0 28 44 1 6 0 0 0 29 39 1 0 0 0 0 29 40 1 0 0 0 0 30 40 1 1 0 0 0 30 41 1 0 0 0 0 31 37 1 0 0 0 0 31 41 1 1 0 0 0 32 37 1 0 0 0 0 32 50 1 6 0 0 0 33 40 1 6 0 0 0 33 48 1 0 0 0 0 34 41 1 6 0 0 0 34 49 1 0 0 0 0 35 38 1 0 0 0 0 35 45 1 1 0 0 0 36 46 2 0 0 0 0 36 50 1 0 0 0 0 38 47 1 0 0 0 0 39 7 1 6 0 0 0 40 8 1 1 0 0 0 41 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	694.41
Volume:	727.01
LogP:	5.642
LogD:	3.91
LogS:	-5.1
# Rotatable Bonds:	8
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	5.468
Fsp3:	0.732
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:	-4.947
MDCK Permeability:	5.8585072110872716e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.086
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.088
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	93.14362335205078%
Volume Distribution (VD):	2.219
Pgp-substrate:	7.038174629211426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.276
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	3.651
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.454
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.429
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.405
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC473602

Natural Product ID:	NPC473602
*Common Name:**	Melianin B
IUPAC Name:	[(1S,3R,5S,7R,8R,9R,10S,13S,17S)-1,7-diacetyloxy-17-[(5R,6S)-5,6-dihydroxy-7,7-dimethyloxepan-3-yl]-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
Synonyms:
Standard InCHIKey:	LCWARTZNQSKAAQ-CRGCUESASA-N
Standard InCHI:	InChI=1S/C41H58O9/c1-23(42)48-33-20-31-37(3,4)32(50-36(46)25-13-11-10-12-14-25)21-34(49-24(2)43)41(31,9)30-17-18-39(7)27(15-16-29(39)40(30,33)8)26-19-28(44)35(45)38(5,6)47-22-26/h10-14,16,26-28,30-35,44-45H,15,17-22H2,1-9H3/t26?,27-,28+,30-,31-,32+,33+,34-,35-,39-,40-,41+/m0/s1
SMILES:	CC(=O)OC1CC2C(C(CC(C2(C3C1(C4=CCC(C4(CC3)C)C5CC(C(C(OC5)(C)C)O)O)C)C)OC(=O)C)OC(=O)C6=CC=CC=C6)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446959
PubChem CID:	44566528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217705]
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461654]
NPO4571	Melia volkensii	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
ED50	6
Others	2

Activity Type	# Activity
Cell Line	6
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.68	ug ml-1	PMID[509810]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.29	ug ml-1	PMID[509810]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.15	ug ml-1	PMID[509810]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	3.67	ug ml-1	PMID[509810]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	3.93	10'-1 ug/ml	PMID[509810]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	2.09	ug ml-1	PMID[509810]
NPT140	Organism	Artemia	Artemia	LC50	>	100.0	ug.mL-1	PMID[509810]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC50	>	100.0	ug.mL-1	PMID[509810]

☑ 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 NPC473602 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	317
0.1-0.2	1126
0.2-0.3	2409
0.3-0.4	4658
0.4-0.5	9414
0.5-0.6	12952
0.6-0.7	9979
0.7-0.8	1428
0.8-0.85	211
0.85-0.9	194
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC473088
0.9362	High Similarity	NPC472575
0.9362	High Similarity	NPC158663
0.9362	High Similarity	NPC476973
0.9362	High Similarity	NPC174982
0.9362	High Similarity	NPC472572
0.9362	High Similarity	NPC184817
0.9362	High Similarity	NPC470159
0.9362	High Similarity	NPC70403
0.9362	High Similarity	NPC96903
0.9362	High Similarity	NPC29704
0.9362	High Similarity	NPC177940
0.9362	High Similarity	NPC472556
0.9362	High Similarity	NPC472568
0.9362	High Similarity	NPC200471
0.9362	High Similarity	NPC471104
0.9362	High Similarity	NPC470157
0.9362	High Similarity	NPC472571
0.9362	High Similarity	NPC469349
0.9362	High Similarity	NPC171525
0.9291	High Similarity	NPC475759
0.9291	High Similarity	NPC95810
0.9291	High Similarity	NPC472570
0.9291	High Similarity	NPC57628
0.9291	High Similarity	NPC70716
0.9291	High Similarity	NPC125106
0.9291	High Similarity	NPC472569
0.9291	High Similarity	NPC241951
0.9291	High Similarity	NPC470152
0.9291	High Similarity	NPC475122
0.9291	High Similarity	NPC188865
0.9291	High Similarity	NPC25768
0.9291	High Similarity	NPC11685
0.9291	High Similarity	NPC163719
0.9291	High Similarity	NPC476974
0.9291	High Similarity	NPC95265
0.9291	High Similarity	NPC472573
0.9286	High Similarity	NPC192658
0.922	High Similarity	NPC163087
0.9214	High Similarity	NPC87448
0.9214	High Similarity	NPC27377
0.9214	High Similarity	NPC97947
0.9214	High Similarity	NPC291599
0.9214	High Similarity	NPC118080
0.9214	High Similarity	NPC266374
0.9214	High Similarity	NPC16912
0.9214	High Similarity	NPC472576
0.9214	High Similarity	NPC41481
0.9167	High Similarity	NPC476975
0.9167	High Similarity	NPC92293
0.9167	High Similarity	NPC266265
0.9167	High Similarity	NPC301556
0.9167	High Similarity	NPC471101
0.9167	High Similarity	NPC270590
0.9155	High Similarity	NPC34943
0.9143	High Similarity	NPC90614
0.9143	High Similarity	NPC97667
0.9143	High Similarity	NPC275592
0.9143	High Similarity	NPC472547
0.9143	High Similarity	NPC87934
0.9143	High Similarity	NPC162613
0.9143	High Similarity	NPC171207
0.9143	High Similarity	NPC100913
0.9103	High Similarity	NPC31829
0.9103	High Similarity	NPC470245
0.9103	High Similarity	NPC473214
0.9097	High Similarity	NPC473760
0.9097	High Similarity	NPC281717
0.9085	High Similarity	NPC91703
0.9078	High Similarity	NPC224491
0.9071	High Similarity	NPC9905
0.9058	High Similarity	NPC48929
0.9048	High Similarity	NPC472658
0.9048	High Similarity	NPC472657
0.9041	High Similarity	NPC470153
0.9034	High Similarity	NPC473215
0.9028	High Similarity	NPC474935
0.9028	High Similarity	NPC20255
0.9028	High Similarity	NPC209592
0.9028	High Similarity	NPC240115
0.9028	High Similarity	NPC48599
0.9014	High Similarity	NPC34012
0.9007	High Similarity	NPC476094
0.9007	High Similarity	NPC473085
0.9007	High Similarity	NPC184747
0.9007	High Similarity	NPC4341
0.9007	High Similarity	NPC473112
0.9007	High Similarity	NPC48017
0.9007	High Similarity	NPC200592
0.9007	High Similarity	NPC473613
0.9007	High Similarity	NPC147880
0.9007	High Similarity	NPC473109
0.9007	High Similarity	NPC473081
0.9007	High Similarity	NPC211137
0.9007	High Similarity	NPC43241
0.9007	High Similarity	NPC473758
0.9007	High Similarity	NPC473060
0.9	High Similarity	NPC475373
0.9	High Similarity	NPC39549
0.898	High Similarity	NPC477905
0.8973	High Similarity	NPC476173
0.8973	High Similarity	NPC7095
0.8966	High Similarity	NPC327031
0.8958	High Similarity	NPC125882
0.8958	High Similarity	NPC311825
0.8958	High Similarity	NPC92867
0.8951	High Similarity	NPC95449
0.8936	High Similarity	NPC475652
0.8936	High Similarity	NPC210591
0.8936	High Similarity	NPC214550
0.8929	High Similarity	NPC472545
0.8929	High Similarity	NPC472551
0.8904	High Similarity	NPC76103
0.8904	High Similarity	NPC250046
0.8904	High Similarity	NPC60509
0.8904	High Similarity	NPC81698
0.8897	High Similarity	NPC312393
0.8897	High Similarity	NPC475552
0.8881	High Similarity	NPC472546
0.8865	High Similarity	NPC283375
0.8865	High Similarity	NPC183122
0.8859	High Similarity	NPC473632
0.8859	High Similarity	NPC473611
0.8859	High Similarity	NPC469730
0.8859	High Similarity	NPC132599
0.8857	High Similarity	NPC472577
0.8857	High Similarity	NPC66761
0.8857	High Similarity	NPC291638
0.8857	High Similarity	NPC17877
0.8857	High Similarity	NPC195647
0.8851	High Similarity	NPC472548
0.8844	High Similarity	NPC165260
0.8844	High Similarity	NPC161239
0.8844	High Similarity	NPC112216
0.8844	High Similarity	NPC198455
0.8819	High Similarity	NPC246480
0.8819	High Similarity	NPC475429
0.8819	High Similarity	NPC139067
0.8819	High Similarity	NPC191082
0.8819	High Similarity	NPC270498
0.8819	High Similarity	NPC473673
0.8819	High Similarity	NPC477894
0.8819	High Similarity	NPC147217
0.8819	High Similarity	NPC177340
0.8808	High Similarity	NPC476784
0.88	High Similarity	NPC106895
0.8794	High Similarity	NPC472372
0.8794	High Similarity	NPC472374
0.8792	High Similarity	NPC249471
0.8792	High Similarity	NPC158333
0.8792	High Similarity	NPC473414
0.8792	High Similarity	NPC304876
0.8792	High Similarity	NPC472005
0.8792	High Similarity	NPC237549
0.8792	High Similarity	NPC472022
0.8792	High Similarity	NPC472030
0.8792	High Similarity	NPC1173
0.8792	High Similarity	NPC265395
0.8792	High Similarity	NPC257213
0.8792	High Similarity	NPC242262
0.8792	High Similarity	NPC256142
0.8786	High Similarity	NPC474608
0.8784	High Similarity	NPC96308
0.8776	High Similarity	NPC473403
0.8768	High Similarity	NPC147561
0.8767	High Similarity	NPC478263
0.8759	High Similarity	NPC51314
0.8759	High Similarity	NPC67777
0.8759	High Similarity	NPC470231
0.8759	High Similarity	NPC38696
0.8742	High Similarity	NPC318447
0.8742	High Similarity	NPC322048
0.8733	High Similarity	NPC112523
0.8733	High Similarity	NPC282239
0.8733	High Similarity	NPC228204
0.8733	High Similarity	NPC26033
0.8733	High Similarity	NPC114410
0.8733	High Similarity	NPC472549
0.8725	High Similarity	NPC469647
0.8725	High Similarity	NPC469648
0.8725	High Similarity	NPC138641
0.8725	High Similarity	NPC145649
0.8725	High Similarity	NPC283875
0.8725	High Similarity	NPC233581
0.8725	High Similarity	NPC22571
0.8716	High Similarity	NPC469448
0.8707	High Similarity	NPC132652
0.8699	High Similarity	NPC478264
0.8699	High Similarity	NPC127857
0.8693	High Similarity	NPC476077
0.8686	High Similarity	NPC470753
0.8686	High Similarity	NPC473220
0.8675	High Similarity	NPC217091
0.8675	High Similarity	NPC323001
0.8675	High Similarity	NPC326235
0.8675	High Similarity	NPC11410
0.8667	High Similarity	NPC77719
0.8667	High Similarity	NPC471135
0.8658	High Similarity	NPC51602
0.8658	High Similarity	NPC471103

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 NPC473602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	762
0.2-0.3	1517
0.3-0.4	2840
0.4-0.5	2334
0.5-0.6	1143
0.6-0.7	273
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8322	Intermediate Similarity	NPD7236	Approved
0.817	Intermediate Similarity	NPD7239	Suspended
0.8037	Intermediate Similarity	NPD7799	Discontinued
0.7771	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD8127	Discontinued
0.7702	Intermediate Similarity	NPD7058	Phase 2
0.7702	Intermediate Similarity	NPD7057	Phase 3
0.7643	Intermediate Similarity	NPD7741	Discontinued
0.7635	Intermediate Similarity	NPD7961	Discontinued
0.7529	Intermediate Similarity	NPD8368	Discontinued
0.75	Intermediate Similarity	NPD8407	Phase 2
0.75	Intermediate Similarity	NPD7008	Discontinued
0.7468	Intermediate Similarity	NPD6273	Approved
0.7457	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8361	Approved
0.7429	Intermediate Similarity	NPD8435	Approved
0.7429	Intermediate Similarity	NPD8360	Approved
0.7415	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8434	Phase 2
0.7372	Intermediate Similarity	NPD8166	Discontinued
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7357	Intermediate Similarity	NPD2629	Approved
0.7305	Intermediate Similarity	NPD4198	Discontinued
0.7278	Intermediate Similarity	NPD8485	Approved
0.7237	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7610	Discontinued
0.7158	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7123	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8150	Discontinued
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7113	Intermediate Similarity	NPD5951	Approved
0.7105	Intermediate Similarity	NPD3764	Approved
0.7071	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5125	Phase 3
0.7055	Intermediate Similarity	NPD5126	Approved
0.7052	Intermediate Similarity	NPD5844	Phase 1
0.7048	Intermediate Similarity	NPD5761	Phase 2
0.7048	Intermediate Similarity	NPD7819	Suspended
0.7048	Intermediate Similarity	NPD8455	Phase 2
0.7048	Intermediate Similarity	NPD5760	Phase 2
0.7044	Intermediate Similarity	NPD7003	Approved
0.7043	Intermediate Similarity	NPD7497	Discontinued
0.7029	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD37	Approved
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6858	Approved
0.6972	Remote Similarity	NPD7094	Approved
0.697	Remote Similarity	NPD4380	Phase 2
0.6964	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7768	Phase 2
0.6964	Remote Similarity	NPD4965	Approved
0.6964	Remote Similarity	NPD4967	Phase 2
0.6964	Remote Similarity	NPD4966	Approved
0.6948	Remote Similarity	NPD6663	Approved
0.6946	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6765	Approved
0.6932	Remote Similarity	NPD6764	Approved
0.6929	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2182	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6909	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5736	Approved
0.6897	Remote Similarity	NPD7228	Approved
0.6882	Remote Similarity	NPD6234	Discontinued
0.6875	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6599	Discontinued
0.6855	Remote Similarity	NPD5762	Approved
0.6855	Remote Similarity	NPD5763	Approved
0.6851	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7473	Discontinued
0.6831	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8320	Phase 1
0.6825	Remote Similarity	NPD8319	Approved
0.6807	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5402	Approved
0.6802	Remote Similarity	NPD7199	Phase 2
0.6792	Remote Similarity	NPD5404	Approved
0.6792	Remote Similarity	NPD5406	Approved
0.6792	Remote Similarity	NPD5408	Approved
0.6792	Remote Similarity	NPD5405	Approved
0.6788	Remote Similarity	NPD5403	Approved
0.6786	Remote Similarity	NPD6801	Discontinued
0.6778	Remote Similarity	NPD6784	Approved
0.6778	Remote Similarity	NPD6785	Approved
0.6774	Remote Similarity	NPD7699	Phase 2
0.6774	Remote Similarity	NPD7700	Phase 2
0.6772	Remote Similarity	NPD7097	Phase 1
0.677	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5401	Approved
0.6768	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6232	Discontinued
0.6759	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6355	Discontinued
0.675	Remote Similarity	NPD7266	Discontinued
0.6742	Remote Similarity	NPD7240	Approved
0.6742	Remote Similarity	NPD6559	Discontinued
0.6733	Remote Similarity	NPD6287	Discontinued
0.6731	Remote Similarity	NPD7715	Approved
0.6731	Remote Similarity	NPD8032	Phase 2
0.6731	Remote Similarity	NPD7714	Approved
0.673	Remote Similarity	NPD2799	Discontinued
0.6728	Remote Similarity	NPD3750	Approved
0.6726	Remote Similarity	NPD7411	Suspended
0.6725	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3226	Approved
0.6703	Remote Similarity	NPD6534	Approved
0.6703	Remote Similarity	NPD6535	Approved
0.6691	Remote Similarity	NPD6647	Phase 2
0.6688	Remote Similarity	NPD4140	Approved
0.6686	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6685	Approved
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6005	Phase 3
0.6646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6002	Phase 3
0.6646	Remote Similarity	NPD2346	Discontinued
0.6646	Remote Similarity	NPD230	Phase 1
0.6643	Remote Similarity	NPD164	Approved
0.6629	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3748	Approved
0.6625	Remote Similarity	NPD7305	Phase 1
0.6624	Remote Similarity	NPD7713	Phase 3
0.6609	Remote Similarity	NPD6959	Discontinued
0.6608	Remote Similarity	NPD3817	Phase 2
0.6606	Remote Similarity	NPD6799	Approved
0.6603	Remote Similarity	NPD7095	Approved
0.6599	Remote Similarity	NPD7115	Discovery
0.6594	Remote Similarity	NPD1238	Approved
0.6591	Remote Similarity	NPD6166	Phase 2
0.6591	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2438	Suspended
0.6584	Remote Similarity	NPD2935	Discontinued
0.6582	Remote Similarity	NPD8462	Phase 1
0.6579	Remote Similarity	NPD7507	Approved
0.6577	Remote Similarity	NPD9545	Approved
0.6577	Remote Similarity	NPD7009	Phase 2
0.6571	Remote Similarity	NPD1929	Approved
0.6571	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1930	Approved
0.6568	Remote Similarity	NPD7028	Phase 2
0.6566	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7874	Approved
0.6564	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6798	Discontinued
0.6558	Remote Similarity	NPD3094	Phase 2
0.6558	Remote Similarity	NPD7319	Approved
0.6552	Remote Similarity	NPD5494	Approved
0.655	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6823	Phase 2
0.6543	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5735	Approved
0.6536	Remote Similarity	NPD7876	Discontinued
0.6536	Remote Similarity	NPD7074	Phase 3
0.6529	Remote Similarity	NPD6677	Suspended
0.6528	Remote Similarity	NPD2067	Discontinued
0.6526	Remote Similarity	NPD6782	Approved
0.6526	Remote Similarity	NPD6778	Approved
0.6526	Remote Similarity	NPD6779	Approved
0.6526	Remote Similarity	NPD6780	Approved
0.6526	Remote Similarity	NPD6776	Approved
0.6526	Remote Similarity	NPD6781	Approved
0.6526	Remote Similarity	NPD6777	Approved
0.6524	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4110	Phase 3
0.6519	Remote Similarity	NPD6233	Phase 2
0.6517	Remote Similarity	NPD3818	Discontinued
0.6516	Remote Similarity	NPD6085	Phase 2
0.6516	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4806	Approved
0.6513	Remote Similarity	NPD4807	Approved
0.6512	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7698	Approved
0.651	Remote Similarity	NPD7697	Approved
0.651	Remote Similarity	NPD7696	Phase 3
0.6506	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD970	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6653	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