NPASS Compound

Structure

NPC221352 OpenBabel07101719512D 57 60 0 0 1 0 0 0 0 0999 V2000 3.9820 8.5145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0322 -0.8064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1448 6.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1761 5.3204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5435 -1.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7389 7.8275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2701 0.5938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7516 5.0059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8639 5.8639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7866 -0.6251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0673 8.7375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4004 0.5515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9635 3.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7013 2.2676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4910 9.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7634 1.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8246 0.6227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6675 7.6155 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5255 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3384 5.8639 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2771 5.0059 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8581 -0.4132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7866 7.8275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8639 1.3384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7516 2.1965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9635 4.0774 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4195 9.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3501 0.6227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2378 1.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2103 8.3137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2269 2.2676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8749 0.5515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2701 6.6085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7389 -0.6251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8581 7.6155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2771 2.1965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3384 1.3384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.2023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4891 3.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7446 0.5938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9099 4.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7002 10.3458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8866 -0.1642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1876 1.5519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6467 7.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0533 3.9838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0485 -1.1646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9436 7.2820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8456 -1.5715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5067 8.0087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4355 3.0183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4180 -0.0796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5255 7.2023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6675 -0.4132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7446 6.6085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4891 4.0774 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 6 18 1 0 0 0 0 6 23 1 0 0 0 0 7 19 1 0 0 0 0 7 24 1 0 0 0 0 8 20 1 0 0 0 0 8 26 1 0 0 0 0 9 21 1 0 0 0 0 9 33 1 0 0 0 0 10 22 1 0 0 0 0 10 34 1 0 0 0 0 11 23 2 0 0 0 0 11 27 1 0 0 0 0 12 24 2 0 0 0 0 12 28 1 0 0 0 0 13 25 1 0 0 0 0 13 26 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 15 27 2 0 0 0 0 15 30 1 0 0 0 0 16 28 2 0 0 0 0 16 31 1 0 0 0 0 17 29 2 0 0 0 0 17 32 1 0 0 0 0 18 1 1 1 0 0 0 18 53 1 0 0 0 0 19 2 1 1 0 0 0 19 54 1 0 0 0 0 20 3 1 1 0 0 0 20 55 1 0 0 0 0 21 4 1 1 0 0 0 21 56 1 0 0 0 0 22 5 1 1 0 0 0 22 57 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 26 41 1 6 0 0 0 27 42 1 0 0 0 0 28 43 1 0 0 0 0 29 44 1 0 0 0 0 30 35 2 0 0 0 0 30 45 1 0 0 0 0 31 36 2 0 0 0 0 31 46 1 0 0 0 0 32 37 2 0 0 0 0 32 47 1 0 0 0 0 33 48 2 0 0 0 0 33 53 1 0 0 0 0 34 49 2 0 0 0 0 34 54 1 0 0 0 0 35 38 1 0 0 0 0 36 39 1 0 0 0 0 37 40 1 0 0 0 0 38 50 2 0 0 0 0 38 55 1 0 0 0 0 39 51 2 0 0 0 0 39 56 1 0 0 0 0 40 52 2 0 0 0 0 40 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	798.27
Volume:	778.693
LogP:	5.683
LogD:	2.741
LogS:	-3.425
# Rotatable Bonds:	0
TPSA:	273.11
# H-Bond Aceptor:	17
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	5.332
Fsp3:	0.425
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.004
MDCK Permeability:	4.91174723720178e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	99.96797943115234%
Volume Distribution (VD):	0.493
Pgp-substrate:	1.8472015857696533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.881
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.883
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.961
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.96
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	10.558
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.814
Carcinogencity:	0.896
Eye Corrosion:	0.003
Eye Irritation:	0.117
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC221352

Natural Product ID:	NPC221352
*Common Name:**	Menisporopsin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MZOGTSLLZCHVTJ-ACLVMWMJSA-N
Standard InCHI:	InChI=1S/C40H46O17/c1-18-6-23-11-27(42)15-30(45)35(23)38(50)55-20(3)8-26(41)13-25-14-29(44)17-32(47)37(25)40(52)57-22(5)10-34(49)54-19(2)7-24-12-28(43)16-31(46)36(24)39(51)56-21(4)9-33(48)53-18/h11-12,14-22,26,41-47H,6-10,13H2,1-5H3/t18-,19-,20-,21-,22-,26-/m1/s1
SMILES:	C[C@@H]1Cc2cc(cc(c2C(=O)O[C@H](C)C[C@H](Cc2cc(cc(c2C(=O)O[C@H](C)CC(=O)O[C@H](C)Cc2cc(cc(c2C(=O)O[C@H](C)CC(=O)O1)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450847
PubChem CID:	5276743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[15104506]
NPO3171	Menisporopsis theobromae	Species	n.a.	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	3
MIC	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.0	ug.mL-1	PMID[486201]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	4.0	ug.mL-1	PMID[486201]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[486201]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.0	ug.mL-1	PMID[486201]

☑ 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 NPC221352 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	327
0.1-0.2	1336
0.2-0.3	2874
0.3-0.4	7042
0.4-0.5	11497
0.5-0.6	4511
0.6-0.7	6051
0.7-0.8	7255
0.8-0.85	1537
0.85-0.9	226
0.9-0.95	39
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC475460
0.9384	High Similarity	NPC476684
0.9291	High Similarity	NPC94248
0.9291	High Similarity	NPC212693
0.9231	High Similarity	NPC53649
0.922	High Similarity	NPC70380
0.9189	High Similarity	NPC309979
0.9189	High Similarity	NPC307780
0.9161	High Similarity	NPC155205
0.9155	High Similarity	NPC191835
0.9155	High Similarity	NPC472602
0.9097	High Similarity	NPC472604
0.9097	High Similarity	NPC158634
0.9097	High Similarity	NPC472605
0.9091	High Similarity	NPC32360
0.9091	High Similarity	NPC139634
0.9091	High Similarity	NPC105456
0.9085	High Similarity	NPC71256
0.9048	High Similarity	NPC473023
0.9028	High Similarity	NPC472600
0.9028	High Similarity	NPC158472
0.9028	High Similarity	NPC472601
0.9021	High Similarity	NPC478200
0.9021	High Similarity	NPC33144
0.9014	High Similarity	NPC235115
0.8986	High Similarity	NPC12305
0.8973	High Similarity	NPC471731
0.8973	High Similarity	NPC478202
0.8973	High Similarity	NPC159721
0.8973	High Similarity	NPC469542
0.8973	High Similarity	NPC51106
0.8966	High Similarity	NPC1704
0.8966	High Similarity	NPC478217
0.8966	High Similarity	NPC472603
0.8966	High Similarity	NPC313123
0.8966	High Similarity	NPC67650
0.8958	High Similarity	NPC268052
0.8954	High Similarity	NPC257309
0.8951	High Similarity	NPC194579
0.8951	High Similarity	NPC301915
0.8951	High Similarity	NPC261292
0.8936	High Similarity	NPC153783
0.8919	High Similarity	NPC237208
0.8912	High Similarity	NPC42540
0.8912	High Similarity	NPC151607
0.8904	High Similarity	NPC250755
0.8904	High Similarity	NPC469579
0.8904	High Similarity	NPC471733
0.8904	High Similarity	NPC474385
0.8889	High Similarity	NPC475974
0.8851	High Similarity	NPC83272
0.8851	High Similarity	NPC134621
0.8851	High Similarity	NPC29577
0.8844	High Similarity	NPC472006
0.8844	High Similarity	NPC472610
0.8836	High Similarity	NPC478201
0.8836	High Similarity	NPC244923
0.8836	High Similarity	NPC472035
0.8828	High Similarity	NPC88269
0.8819	High Similarity	NPC178467
0.8819	High Similarity	NPC149372
0.8819	High Similarity	NPC65837
0.8819	High Similarity	NPC474771
0.8819	High Similarity	NPC474849
0.8811	High Similarity	NPC142027
0.8808	High Similarity	NPC60413
0.8794	High Similarity	NPC189823
0.8794	High Similarity	NPC219892
0.8792	High Similarity	NPC470570
0.8784	High Similarity	NPC210425
0.8784	High Similarity	NPC66404
0.8784	High Similarity	NPC277426
0.8784	High Similarity	NPC86373
0.8784	High Similarity	NPC280404
0.8784	High Similarity	NPC95123
0.8767	High Similarity	NPC275903
0.8766	High Similarity	NPC146211
0.875	High Similarity	NPC215921
0.875	High Similarity	NPC70016
0.8742	High Similarity	NPC237440
0.8742	High Similarity	NPC270160
0.8742	High Similarity	NPC6923
0.8741	High Similarity	NPC175943
0.8734	High Similarity	NPC7752
0.8733	High Similarity	NPC476463
0.8733	High Similarity	NPC81835
0.8733	High Similarity	NPC125801
0.8733	High Similarity	NPC471734
0.8732	High Similarity	NPC476389
0.8725	High Similarity	NPC257558
0.8725	High Similarity	NPC34482
0.8718	High Similarity	NPC472055
0.8707	High Similarity	NPC475730
0.8699	High Similarity	NPC112789
0.8699	High Similarity	NPC247409
0.8699	High Similarity	NPC19622
0.8699	High Similarity	NPC474655
0.8693	High Similarity	NPC273483
0.8693	High Similarity	NPC167903
0.8693	High Similarity	NPC478224
0.869	High Similarity	NPC135837
0.8684	High Similarity	NPC469670
0.8684	High Similarity	NPC469619
0.8684	High Similarity	NPC56204
0.8681	High Similarity	NPC27407
0.8675	High Similarity	NPC106328
0.8675	High Similarity	NPC240253
0.8675	High Similarity	NPC35150
0.8675	High Similarity	NPC471642
0.8675	High Similarity	NPC240622
0.8675	High Similarity	NPC471641
0.8667	High Similarity	NPC267509
0.8667	High Similarity	NPC471735
0.8667	High Similarity	NPC163846
0.8667	High Similarity	NPC107625
0.8667	High Similarity	NPC225173
0.8658	High Similarity	NPC210966
0.8658	High Similarity	NPC48762
0.8658	High Similarity	NPC478203
0.8658	High Similarity	NPC126882
0.8654	High Similarity	NPC470339
0.8649	High Similarity	NPC105648
0.8649	High Similarity	NPC474961
0.8649	High Similarity	NPC82913
0.8639	High Similarity	NPC168471
0.863	High Similarity	NPC9121
0.863	High Similarity	NPC472403
0.863	High Similarity	NPC177307
0.8627	High Similarity	NPC240768
0.8627	High Similarity	NPC478148
0.8627	High Similarity	NPC91809
0.8627	High Similarity	NPC470569
0.8627	High Similarity	NPC200773
0.8627	High Similarity	NPC133856
0.8625	High Similarity	NPC249977
0.8621	High Similarity	NPC50455
0.8621	High Similarity	NPC291454
0.8621	High Similarity	NPC158481
0.8618	High Similarity	NPC4423
0.8618	High Similarity	NPC291049
0.8618	High Similarity	NPC77325
0.8618	High Similarity	NPC233267
0.8609	High Similarity	NPC210320
0.8609	High Similarity	NPC472036
0.86	High Similarity	NPC472034
0.86	High Similarity	NPC32470
0.8592	High Similarity	NPC247477
0.8592	High Similarity	NPC17840
0.8591	High Similarity	NPC310340
0.8581	High Similarity	NPC69043
0.8581	High Similarity	NPC89625
0.8581	High Similarity	NPC220106
0.8581	High Similarity	NPC37530
0.8581	High Similarity	NPC478230
0.8581	High Similarity	NPC149618
0.8571	High Similarity	NPC275356
0.8571	High Similarity	NPC474843
0.8571	High Similarity	NPC52358
0.8571	High Similarity	NPC43345
0.8571	High Similarity	NPC92655
0.8562	High Similarity	NPC164762
0.8562	High Similarity	NPC470568
0.8562	High Similarity	NPC477835
0.8562	High Similarity	NPC472891
0.8562	High Similarity	NPC205766
0.8553	High Similarity	NPC73411
0.8553	High Similarity	NPC2569
0.8553	High Similarity	NPC215711
0.8553	High Similarity	NPC172329
0.8553	High Similarity	NPC105415
0.8552	High Similarity	NPC180905
0.8552	High Similarity	NPC182496
0.8544	High Similarity	NPC69868
0.8543	High Similarity	NPC202112
0.8543	High Similarity	NPC472033
0.8543	High Similarity	NPC25844
0.8543	High Similarity	NPC51513
0.8533	High Similarity	NPC470932
0.8533	High Similarity	NPC21599
0.8533	High Similarity	NPC193703
0.8531	High Similarity	NPC214702
0.8531	High Similarity	NPC470831
0.8526	High Similarity	NPC227062
0.8526	High Similarity	NPC471787
0.8523	High Similarity	NPC137649
0.8523	High Similarity	NPC135524
0.8523	High Similarity	NPC49108
0.8516	High Similarity	NPC137301
0.8516	High Similarity	NPC472799
0.8516	High Similarity	NPC470102
0.8516	High Similarity	NPC478231
0.8514	High Similarity	NPC99441
0.8514	High Similarity	NPC64664
0.8514	High Similarity	NPC470986
0.8509	High Similarity	NPC76647
0.8506	High Similarity	NPC78835
0.8506	High Similarity	NPC476553
0.8506	High Similarity	NPC476552
0.8506	High Similarity	NPC474417
0.8506	High Similarity	NPC204561

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 NPC221352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	893
0.2-0.3	1557
0.3-0.4	2590
0.4-0.5	2049
0.5-0.6	1186
0.6-0.7	410
0.7-0.8	148
0.8-0.85	29
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD970	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8291	Intermediate Similarity	NPD7768	Phase 2
0.8269	Intermediate Similarity	NPD7411	Suspended
0.8239	Intermediate Similarity	NPD7075	Discontinued
0.8235	Intermediate Similarity	NPD2532	Approved
0.8235	Intermediate Similarity	NPD2533	Approved
0.8235	Intermediate Similarity	NPD2534	Approved
0.8176	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD7390	Discontinued
0.816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1510	Phase 2
0.8121	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD4380	Phase 2
0.8079	Intermediate Similarity	NPD1549	Phase 2
0.805	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1934	Approved
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7974	Intermediate Similarity	NPD3750	Approved
0.7973	Intermediate Similarity	NPD1240	Approved
0.7959	Intermediate Similarity	NPD3764	Approved
0.7947	Intermediate Similarity	NPD2796	Approved
0.7947	Intermediate Similarity	NPD5405	Approved
0.7947	Intermediate Similarity	NPD5404	Approved
0.7947	Intermediate Similarity	NPD5406	Approved
0.7947	Intermediate Similarity	NPD5408	Approved
0.7917	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD3817	Phase 2
0.7867	Intermediate Similarity	NPD1607	Approved
0.7857	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD7074	Phase 3
0.7838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.7824	Intermediate Similarity	NPD7808	Phase 3
0.7821	Intermediate Similarity	NPD6799	Approved
0.78	Intermediate Similarity	NPD230	Phase 1
0.7798	Intermediate Similarity	NPD7054	Approved
0.7798	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD6599	Discontinued
0.7746	Intermediate Similarity	NPD8150	Discontinued
0.7738	Intermediate Similarity	NPD3818	Discontinued
0.7716	Intermediate Similarity	NPD2801	Approved
0.7712	Intermediate Similarity	NPD1551	Phase 2
0.7707	Intermediate Similarity	NPD1511	Approved
0.7706	Intermediate Similarity	NPD6797	Phase 2
0.7688	Intermediate Similarity	NPD3226	Approved
0.7674	Intermediate Similarity	NPD8312	Approved
0.7674	Intermediate Similarity	NPD8313	Approved
0.7673	Intermediate Similarity	NPD5403	Approved
0.7669	Intermediate Similarity	NPD5402	Approved
0.7661	Intermediate Similarity	NPD6559	Discontinued
0.7658	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD7199	Phase 2
0.7647	Intermediate Similarity	NPD3748	Approved
0.7628	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD3882	Suspended
0.7622	Intermediate Similarity	NPD4966	Approved
0.7622	Intermediate Similarity	NPD4967	Phase 2
0.7622	Intermediate Similarity	NPD8151	Discontinued
0.7622	Intermediate Similarity	NPD4965	Approved
0.7616	Intermediate Similarity	NPD943	Approved
0.7616	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1512	Approved
0.7607	Intermediate Similarity	NPD1465	Phase 2
0.7605	Intermediate Similarity	NPD5710	Approved
0.7605	Intermediate Similarity	NPD5711	Approved
0.7586	Intermediate Similarity	NPD1201	Approved
0.758	Intermediate Similarity	NPD6190	Approved
0.7578	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD9545	Approved
0.7547	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD7229	Phase 3
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7456	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7228	Approved
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7413	Intermediate Similarity	NPD9493	Approved
0.7403	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5953	Discontinued
0.7381	Intermediate Similarity	NPD5494	Approved
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7342	Intermediate Similarity	NPD1243	Approved
0.7342	Intermediate Similarity	NPD2800	Approved
0.7325	Intermediate Similarity	NPD2346	Discontinued
0.7312	Intermediate Similarity	NPD8320	Phase 1
0.7312	Intermediate Similarity	NPD8319	Approved
0.7308	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD7003	Approved
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7284	Intermediate Similarity	NPD6273	Approved
0.7283	Intermediate Similarity	NPD7286	Phase 2
0.7268	Intermediate Similarity	NPD7699	Phase 2
0.7268	Intermediate Similarity	NPD7700	Phase 2
0.7267	Intermediate Similarity	NPD1164	Approved
0.7267	Intermediate Similarity	NPD1203	Approved
0.7263	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7783	Phase 2
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.7239	Intermediate Similarity	NPD920	Approved
0.7219	Intermediate Similarity	NPD7870	Phase 2
0.7219	Intermediate Similarity	NPD7871	Phase 2
0.7216	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2344	Approved
0.7208	Intermediate Similarity	NPD6663	Approved
0.7205	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6535	Approved
0.7198	Intermediate Similarity	NPD6534	Approved
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8166	Discontinued
0.7181	Intermediate Similarity	NPD1608	Approved
0.7171	Intermediate Similarity	NPD5736	Approved
0.7166	Intermediate Similarity	NPD7698	Approved
0.7166	Intermediate Similarity	NPD7696	Phase 3
0.7166	Intermediate Similarity	NPD7697	Approved
0.7159	Intermediate Similarity	NPD7240	Approved
0.7152	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.712	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7874	Approved
0.7118	Intermediate Similarity	NPD919	Approved
0.7117	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7266	Discontinued
0.7105	Intermediate Similarity	NPD2798	Approved
0.7097	Intermediate Similarity	NPD6776	Approved
0.7097	Intermediate Similarity	NPD6777	Approved
0.7097	Intermediate Similarity	NPD6782	Approved
0.7097	Intermediate Similarity	NPD6781	Approved
0.7097	Intermediate Similarity	NPD6780	Approved
0.7097	Intermediate Similarity	NPD6778	Approved
0.7097	Intermediate Similarity	NPD6779	Approved
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7072	Intermediate Similarity	NPD4287	Approved
0.7067	Intermediate Similarity	NPD9717	Approved
0.7067	Intermediate Similarity	NPD9269	Phase 2
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7685	Pre-registration
0.7037	Intermediate Similarity	NPD2309	Approved
0.7032	Intermediate Similarity	NPD2313	Discontinued
0.7027	Intermediate Similarity	NPD9268	Approved
0.7016	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7005	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD422	Phase 1
0.6981	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD17	Approved
0.6977	Remote Similarity	NPD6746	Phase 2
0.6974	Remote Similarity	NPD1283	Approved
0.6968	Remote Similarity	NPD3027	Phase 3
0.6968	Remote Similarity	NPD4625	Phase 3
0.6959	Remote Similarity	NPD6971	Discontinued
0.6957	Remote Similarity	NPD6213	Phase 3
0.6957	Remote Similarity	NPD6212	Phase 3
0.6957	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4060	Phase 1
0.6943	Remote Similarity	NPD1613	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