NPASS Compound

Structure

NPC312824 OpenBabel07101719252D 34 39 0 0 1 0 0 0 0 0999 V2000 -7.1527 3.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 5.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 4.2248 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 -7.7707 5.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 4.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 4.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7926 5.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 4.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1235 6.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0798 6.5428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -6.4325 7.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 5.9190 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 1 14 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 18 2 0 0 0 0 6 19 1 0 0 0 0 7 8 2 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 26 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 17 2 0 0 0 0 15 2 1 1 0 0 0 15 18 1 0 0 0 0 16 12 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 26 1 6 0 0 0 20 27 1 6 0 0 0 21 15 1 1 0 0 0 21 33 1 0 0 0 0 22 27 1 0 0 0 0 22 30 2 0 0 0 0 23 28 1 6 0 0 0 23 31 1 0 0 0 0 24 28 1 6 0 0 0 24 34 1 0 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.25
Volume:	481.064
LogP:	3.569
LogD:	3.197
LogS:	-4.418
# Rotatable Bonds:	3
TPSA:	93.2
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	5.867
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.014
MDCK Permeability:	1.7503791241324507e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.31

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	72.4692611694336%
Volume Distribution (VD):	0.947
Pgp-substrate:	14.69151496887207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.425
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.899

ADMET: Excretion

Clearance (CL):	16.131
Half-life (T1/2):	0.715

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.176
Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.542
Carcinogencity:	0.852
Eye Corrosion:	0.059
Eye Irritation:	0.241
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC312824

Natural Product ID:	NPC312824
*Common Name:**	Witharistatin
IUPAC Name:	n.a.
Synonyms:	Witharistatin
Standard InCHIKey:	UFEAJHDMQVGVJI-NODKRQMBSA-N
Standard InCHI:	InChI=1S/C28H36O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h5,7-8,15-16,19-21,23-24,29,31H,6,9-13H2,1-4H3/t15-,16-,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
SMILES:	CC1=C(CO)C(=O)O[C@H](C1)[C@@H](C)C1=CC[C@H]2[C@@H]3C[C@@H]4[C@@]5([C@H](C=CC(=O)[C@]5(C)[C@H]3CC[C@]12C)O)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047411
PubChem CID:	70690364
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and 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
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22705001]
NPO20281	Withania aristata	Species	Solanaceae	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	8
Others	2

Activity Type	# Activity
Cell Line	9
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3500.0	nM	PMID[496791]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4200.0	nM	PMID[496791]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2700.0	nM	PMID[496791]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2300.0	nM	PMID[496791]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1200.0	nM	PMID[496791]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	300.0	nM	PMID[496791]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	3400.0	nM	PMID[496791]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	2600.0	nM	PMID[496791]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	2.8	n.a.	PMID[496791]
NPT979	Individual Protein	Caspase-3	Homo sapiens	FC	=	1.0	n.a.	PMID[496791]

☑ 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 NPC312824 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	233
0.1-0.2	1299
0.2-0.3	3759
0.3-0.4	7195
0.4-0.5	13385
0.5-0.6	7855
0.6-0.7	6330
0.7-0.8	2379
0.8-0.85	194
0.85-0.9	49
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470493
1.0	High Similarity	NPC183580
0.9815	High Similarity	NPC167606
0.9815	High Similarity	NPC286528
0.9815	High Similarity	NPC140055
0.9815	High Similarity	NPC20302
0.9725	High Similarity	NPC50774
0.9725	High Similarity	NPC709
0.9636	High Similarity	NPC264954
0.9633	High Similarity	NPC470492
0.955	High Similarity	NPC474370
0.9545	High Similarity	NPC186525
0.9537	High Similarity	NPC122056
0.9464	High Similarity	NPC67569
0.945	High Similarity	NPC67259
0.945	High Similarity	NPC147912
0.9381	High Similarity	NPC153700
0.9381	High Similarity	NPC88326
0.9381	High Similarity	NPC23786
0.9381	High Similarity	NPC470265
0.9298	High Similarity	NPC469789
0.9286	High Similarity	NPC473274
0.9259	High Similarity	NPC29133
0.9217	High Similarity	NPC8374
0.9217	High Similarity	NPC8369
0.9217	High Similarity	NPC470494
0.9217	High Similarity	NPC3381
0.9189	High Similarity	NPC270929
0.9189	High Similarity	NPC64318
0.9174	High Similarity	NPC470961
0.9138	High Similarity	NPC293112
0.913	High Similarity	NPC11895
0.9123	High Similarity	NPC470878
0.9123	High Similarity	NPC473256
0.9107	High Similarity	NPC243065
0.9052	High Similarity	NPC81736
0.9052	High Similarity	NPC172154
0.9043	High Similarity	NPC170538
0.9027	High Similarity	NPC329736
0.9	High Similarity	NPC474315
0.8947	High Similarity	NPC61520
0.8929	High Similarity	NPC284915
0.8919	High Similarity	NPC191620
0.8908	High Similarity	NPC473593
0.8814	High Similarity	NPC473635
0.8807	High Similarity	NPC91034
0.8783	High Similarity	NPC473270
0.8772	High Similarity	NPC470959
0.8772	High Similarity	NPC476965
0.876	High Similarity	NPC231240
0.875	High Similarity	NPC69291
0.8739	High Similarity	NPC37116
0.8689	High Similarity	NPC316915
0.8649	High Similarity	NPC475065
0.8636	High Similarity	NPC329048
0.8636	High Similarity	NPC330011
0.8632	High Similarity	NPC46570
0.8621	High Similarity	NPC475520
0.8621	High Similarity	NPC476960
0.8584	High Similarity	NPC236217
0.8583	High Similarity	NPC156797
0.8559	High Similarity	NPC220155
0.8559	High Similarity	NPC269642
0.8559	High Similarity	NPC475418
0.8559	High Similarity	NPC318363
0.8559	High Similarity	NPC107493
0.8559	High Similarity	NPC473482
0.8547	High Similarity	NPC476961
0.8547	High Similarity	NPC268530
0.8547	High Similarity	NPC154491
0.8522	High Similarity	NPC176840
0.8496	Intermediate Similarity	NPC470960
0.8487	Intermediate Similarity	NPC204812
0.8487	Intermediate Similarity	NPC120724
0.8482	Intermediate Similarity	NPC41405
0.8475	Intermediate Similarity	NPC159456
0.8475	Intermediate Similarity	NPC4021
0.8468	Intermediate Similarity	NPC473284
0.8462	Intermediate Similarity	NPC475041
0.8462	Intermediate Similarity	NPC42673
0.8448	Intermediate Similarity	NPC469684
0.8448	Intermediate Similarity	NPC284068
0.8443	Intermediate Similarity	NPC476966
0.843	Intermediate Similarity	NPC287423
0.843	Intermediate Similarity	NPC473253
0.8426	Intermediate Similarity	NPC474012
0.8426	Intermediate Similarity	NPC476299
0.8421	Intermediate Similarity	NPC476163
0.8421	Intermediate Similarity	NPC470063
0.8421	Intermediate Similarity	NPC269530
0.8417	Intermediate Similarity	NPC32868
0.8417	Intermediate Similarity	NPC241456
0.8407	Intermediate Similarity	NPC473627
0.839	Intermediate Similarity	NPC251226
0.839	Intermediate Similarity	NPC476962
0.8376	Intermediate Similarity	NPC257457
0.8376	Intermediate Similarity	NPC311554
0.8376	Intermediate Similarity	NPC473720
0.8374	Intermediate Similarity	NPC196921
0.8374	Intermediate Similarity	NPC220757
0.8364	Intermediate Similarity	NPC475050
0.8364	Intermediate Similarity	NPC264048
0.8362	Intermediate Similarity	NPC470075
0.8361	Intermediate Similarity	NPC473620
0.8349	Intermediate Similarity	NPC476897
0.8348	Intermediate Similarity	NPC25909
0.8333	Intermediate Similarity	NPC278386
0.8333	Intermediate Similarity	NPC316598
0.8333	Intermediate Similarity	NPC159763
0.8333	Intermediate Similarity	NPC474229
0.8333	Intermediate Similarity	NPC124512
0.8333	Intermediate Similarity	NPC478056
0.8333	Intermediate Similarity	NPC317107
0.8319	Intermediate Similarity	NPC472216
0.8319	Intermediate Similarity	NPC87335
0.8319	Intermediate Similarity	NPC5475
0.8319	Intermediate Similarity	NPC173905
0.8319	Intermediate Similarity	NPC284828
0.8305	Intermediate Similarity	NPC230513
0.8304	Intermediate Similarity	NPC67321
0.8304	Intermediate Similarity	NPC471783
0.8304	Intermediate Similarity	NPC301666
0.8304	Intermediate Similarity	NPC187435
0.8304	Intermediate Similarity	NPC9457
0.8293	Intermediate Similarity	NPC231529
0.8293	Intermediate Similarity	NPC470880
0.8293	Intermediate Similarity	NPC35109
0.8291	Intermediate Similarity	NPC55296
0.8291	Intermediate Similarity	NPC471854
0.8279	Intermediate Similarity	NPC287903
0.8276	Intermediate Similarity	NPC474181
0.8273	Intermediate Similarity	NPC469316
0.8261	Intermediate Similarity	NPC317687
0.8246	Intermediate Similarity	NPC5284
0.8246	Intermediate Similarity	NPC239097
0.8241	Intermediate Similarity	NPC73911
0.8241	Intermediate Similarity	NPC253826
0.824	Intermediate Similarity	NPC469673
0.8235	Intermediate Similarity	NPC79579
0.823	Intermediate Similarity	NPC472825
0.823	Intermediate Similarity	NPC306265
0.822	Intermediate Similarity	NPC153440
0.822	Intermediate Similarity	NPC284707
0.8214	Intermediate Similarity	NPC266570
0.8205	Intermediate Similarity	NPC190286
0.8198	Intermediate Similarity	NPC478057
0.8198	Intermediate Similarity	NPC324001
0.8198	Intermediate Similarity	NPC72151
0.8198	Intermediate Similarity	NPC329345
0.8198	Intermediate Similarity	NPC473283
0.8198	Intermediate Similarity	NPC112009
0.8198	Intermediate Similarity	NPC476889
0.8198	Intermediate Similarity	NPC297617
0.8198	Intermediate Similarity	NPC476237
0.8198	Intermediate Similarity	NPC239716
0.8198	Intermediate Similarity	NPC95899
0.8198	Intermediate Similarity	NPC475526
0.8197	Intermediate Similarity	NPC203702
0.8197	Intermediate Similarity	NPC120994
0.819	Intermediate Similarity	NPC255017
0.8182	Intermediate Similarity	NPC303559
0.8182	Intermediate Similarity	NPC282524
0.8182	Intermediate Similarity	NPC473979
0.8175	Intermediate Similarity	NPC476823
0.8174	Intermediate Similarity	NPC324683
0.8174	Intermediate Similarity	NPC470076
0.8165	Intermediate Similarity	NPC98868
0.816	Intermediate Similarity	NPC34963
0.8158	Intermediate Similarity	NPC475941
0.8158	Intermediate Similarity	NPC474901
0.8151	Intermediate Similarity	NPC77689
0.8151	Intermediate Similarity	NPC5292
0.8151	Intermediate Similarity	NPC470495
0.8151	Intermediate Similarity	NPC473636
0.8151	Intermediate Similarity	NPC473203
0.8148	Intermediate Similarity	NPC242848
0.8148	Intermediate Similarity	NPC117133
0.8142	Intermediate Similarity	NPC131665
0.8142	Intermediate Similarity	NPC475176
0.8142	Intermediate Similarity	NPC255387
0.8142	Intermediate Similarity	NPC473165
0.8142	Intermediate Similarity	NPC475294
0.8136	Intermediate Similarity	NPC98249
0.8136	Intermediate Similarity	NPC58662
0.8136	Intermediate Similarity	NPC134430
0.8136	Intermediate Similarity	NPC53396
0.8136	Intermediate Similarity	NPC473656
0.8136	Intermediate Similarity	NPC239273
0.813	Intermediate Similarity	NPC42399
0.813	Intermediate Similarity	NPC473265
0.813	Intermediate Similarity	NPC470882
0.813	Intermediate Similarity	NPC298841
0.8125	Intermediate Similarity	NPC189616
0.8125	Intermediate Similarity	NPC472868
0.8125	Intermediate Similarity	NPC296950
0.8125	Intermediate Similarity	NPC473175
0.8125	Intermediate Similarity	NPC146731
0.812	Intermediate Similarity	NPC238667
0.812	Intermediate Similarity	NPC470953
0.8115	Intermediate Similarity	NPC469790

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 NPC312824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1490
0.2-0.3	3436
0.3-0.4	2548
0.4-0.5	959
0.5-0.6	271
0.6-0.7	185
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9815	High Similarity	NPD7115	Discovery
0.8333	Intermediate Similarity	NPD4225	Approved
0.7797	Intermediate Similarity	NPD8297	Approved
0.7759	Intermediate Similarity	NPD6899	Approved
0.7759	Intermediate Similarity	NPD6881	Approved
0.7712	Intermediate Similarity	NPD6649	Approved
0.7712	Intermediate Similarity	NPD6650	Approved
0.7692	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD5697	Approved
0.7642	Intermediate Similarity	NPD6319	Approved
0.7627	Intermediate Similarity	NPD7102	Approved
0.7627	Intermediate Similarity	NPD7290	Approved
0.7627	Intermediate Similarity	NPD6883	Approved
0.7627	Intermediate Similarity	NPD6371	Approved
0.7611	Intermediate Similarity	NPD7640	Approved
0.7611	Intermediate Similarity	NPD7639	Approved
0.7586	Intermediate Similarity	NPD6402	Approved
0.7586	Intermediate Similarity	NPD5739	Approved
0.7586	Intermediate Similarity	NPD6675	Approved
0.7586	Intermediate Similarity	NPD7128	Approved
0.7563	Intermediate Similarity	NPD6869	Approved
0.7563	Intermediate Similarity	NPD6847	Approved
0.7563	Intermediate Similarity	NPD8130	Phase 1
0.7563	Intermediate Similarity	NPD6617	Approved
0.7545	Intermediate Similarity	NPD6399	Phase 3
0.7542	Intermediate Similarity	NPD6012	Approved
0.7542	Intermediate Similarity	NPD6014	Approved
0.7542	Intermediate Similarity	NPD6372	Approved
0.7542	Intermediate Similarity	NPD6373	Approved
0.7542	Intermediate Similarity	NPD6013	Approved
0.7522	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7479	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5211	Phase 2
0.7477	Intermediate Similarity	NPD7748	Approved
0.7458	Intermediate Similarity	NPD7320	Approved
0.7458	Intermediate Similarity	NPD6011	Approved
0.7455	Intermediate Similarity	NPD6079	Approved
0.7455	Intermediate Similarity	NPD7515	Phase 2
0.7442	Intermediate Similarity	NPD7319	Approved
0.7438	Intermediate Similarity	NPD4632	Approved
0.7434	Intermediate Similarity	NPD7902	Approved
0.7434	Intermediate Similarity	NPD6084	Phase 2
0.7434	Intermediate Similarity	NPD6083	Phase 2
0.7402	Intermediate Similarity	NPD7492	Approved
0.7373	Intermediate Similarity	NPD5701	Approved
0.7364	Intermediate Similarity	NPD7736	Approved
0.7364	Intermediate Similarity	NPD5785	Approved
0.736	Intermediate Similarity	NPD6054	Approved
0.735	Intermediate Similarity	NPD5141	Approved
0.7344	Intermediate Similarity	NPD7507	Approved
0.7344	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD4634	Approved
0.7315	Intermediate Similarity	NPD3618	Phase 1
0.7311	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6686	Approved
0.7304	Intermediate Similarity	NPD4696	Approved
0.7304	Intermediate Similarity	NPD5285	Approved
0.7304	Intermediate Similarity	NPD5286	Approved
0.7302	Intermediate Similarity	NPD7503	Approved
0.7288	Intermediate Similarity	NPD6008	Approved
0.7287	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD5328	Approved
0.7257	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6370	Approved
0.7241	Intermediate Similarity	NPD5344	Discontinued
0.7227	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1694	Approved
0.7217	Intermediate Similarity	NPD5696	Approved
0.7193	Intermediate Similarity	NPD5221	Approved
0.7193	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5222	Approved
0.7188	Intermediate Similarity	NPD7604	Phase 2
0.7179	Intermediate Similarity	NPD4633	Approved
0.7179	Intermediate Similarity	NPD5226	Approved
0.7179	Intermediate Similarity	NPD5225	Approved
0.7179	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7900	Approved
0.7165	Intermediate Similarity	NPD8513	Phase 3
0.7165	Intermediate Similarity	NPD6016	Approved
0.7165	Intermediate Similarity	NPD6015	Approved
0.7156	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD7101	Approved
0.7131	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4755	Approved
0.713	Intermediate Similarity	NPD5173	Approved
0.713	Intermediate Similarity	NPD4786	Approved
0.712	Intermediate Similarity	NPD6009	Approved
0.7119	Intermediate Similarity	NPD5174	Approved
0.7119	Intermediate Similarity	NPD5175	Approved
0.7109	Intermediate Similarity	NPD5988	Approved
0.7105	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4629	Approved
0.7105	Intermediate Similarity	NPD5695	Phase 3
0.7105	Intermediate Similarity	NPD5210	Approved
0.7094	Intermediate Similarity	NPD5223	Approved
0.7091	Intermediate Similarity	NPD3573	Approved
0.7087	Intermediate Similarity	NPD6059	Approved
0.7083	Intermediate Similarity	NPD6412	Phase 2
0.708	Intermediate Similarity	NPD4202	Approved
0.7063	Intermediate Similarity	NPD7328	Approved
0.7063	Intermediate Similarity	NPD6335	Approved
0.7063	Intermediate Similarity	NPD7327	Approved
0.7054	Intermediate Similarity	NPD8328	Phase 3
0.7043	Intermediate Similarity	NPD4697	Phase 3
0.704	Intermediate Similarity	NPD6274	Approved
0.704	Intermediate Similarity	NPD6868	Approved
0.7034	Intermediate Similarity	NPD7632	Discontinued
0.7031	Intermediate Similarity	NPD8517	Approved
0.7031	Intermediate Similarity	NPD8515	Approved
0.7031	Intermediate Similarity	NPD8516	Approved
0.7031	Intermediate Similarity	NPD5983	Phase 2
0.7031	Intermediate Similarity	NPD8033	Approved
0.7027	Intermediate Similarity	NPD5737	Approved
0.7027	Intermediate Similarity	NPD6672	Approved
0.7027	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD8293	Discontinued
0.7009	Intermediate Similarity	NPD4700	Approved
0.7008	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.6991	Remote Similarity	NPD8035	Phase 2
0.6991	Remote Similarity	NPD5693	Phase 1
0.6991	Remote Similarity	NPD6411	Approved
0.6991	Remote Similarity	NPD7637	Suspended
0.6991	Remote Similarity	NPD8034	Phase 2
0.6984	Remote Similarity	NPD6317	Approved
0.6964	Remote Similarity	NPD4753	Phase 2
0.6953	Remote Similarity	NPD8294	Approved
0.6953	Remote Similarity	NPD8377	Approved
0.6947	Remote Similarity	NPD6336	Discontinued
0.6944	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3667	Approved
0.6942	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6053	Discontinued
0.693	Remote Similarity	NPD5779	Approved
0.693	Remote Similarity	NPD5778	Approved
0.6929	Remote Similarity	NPD6314	Approved
0.6929	Remote Similarity	NPD6313	Approved
0.6909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5363	Approved
0.6903	Remote Similarity	NPD46	Approved
0.6903	Remote Similarity	NPD6698	Approved
0.6899	Remote Similarity	NPD8379	Approved
0.6899	Remote Similarity	NPD8335	Approved
0.6899	Remote Similarity	NPD8380	Approved
0.6899	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8296	Approved
0.6899	Remote Similarity	NPD8378	Approved
0.6885	Remote Similarity	NPD4729	Approved
0.6885	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD6903	Approved
0.687	Remote Similarity	NPD6001	Approved
0.6864	Remote Similarity	NPD6648	Approved
0.6847	Remote Similarity	NPD4623	Approved
0.6847	Remote Similarity	NPD4519	Discontinued
0.6842	Remote Similarity	NPD5284	Approved
0.6842	Remote Similarity	NPD5281	Approved
0.6829	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3665	Phase 1
0.6818	Remote Similarity	NPD3666	Approved
0.6818	Remote Similarity	NPD3133	Approved
0.6814	Remote Similarity	NPD6904	Approved
0.6814	Remote Similarity	NPD6673	Approved
0.6814	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6080	Approved
0.6814	Remote Similarity	NPD6101	Approved
0.6774	Remote Similarity	NPD5250	Approved
0.6774	Remote Similarity	NPD5251	Approved
0.6774	Remote Similarity	NPD5247	Approved
0.6774	Remote Similarity	NPD5248	Approved
0.6774	Remote Similarity	NPD5249	Phase 3
0.6769	Remote Similarity	NPD6908	Approved
0.6769	Remote Similarity	NPD6909	Approved
0.6748	Remote Similarity	NPD5128	Approved
0.6746	Remote Similarity	NPD8133	Approved
0.6721	Remote Similarity	NPD4767	Approved
0.6721	Remote Similarity	NPD4768	Approved
0.672	Remote Similarity	NPD5215	Approved
0.672	Remote Similarity	NPD5216	Approved
0.672	Remote Similarity	NPD5217	Approved
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6642	Remote Similarity	NPD8074	Phase 3
0.6641	Remote Similarity	NPD6921	Approved
0.664	Remote Similarity	NPD5169	Approved
0.664	Remote Similarity	NPD5135	Approved
0.664	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4270	Approved
0.6636	Remote Similarity	NPD4269	Approved
0.6636	Remote Similarity	NPD4221	Approved
0.6636	Remote Similarity	NPD4223	Phase 3

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