NPASS Compound

Structure

NPC176840 OpenBabel07101718322D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.8344 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1727 -3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 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 -1.0522 -3.2382 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 0.8660 1.5000 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 -1.5388 -0.5000 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 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -2.8838 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 1.7321 -0.0000 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 -0.9511 -1.3090 0.0000 C 0 0 0 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 -2.2382 -2.4680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8855 -1.9328 0.0000 C 0 0 0 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 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 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 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5546 -1.1896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 18 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 21 2 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 28 1 6 0 0 0 21 25 1 0 0 0 0 21 27 1 0 0 0 0 22 26 1 0 0 0 0 22 29 2 0 0 0 0 23 27 1 1 0 0 0 23 33 1 0 0 0 0 24 30 2 0 0 0 0 24 33 1 0 0 0 0 25 28 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 6 0 0 0 27 31 1 0 0 0 0 28 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.26
Volume:	478.194
LogP:	3.243
LogD:	2.353
LogS:	-4.897
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	5.385
Fsp3:	0.643
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:	-4.736
MDCK Permeability:	2.8090333216823637e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.148
Human Intestinal Absorption (HIA):	0.132
20% Bioavailability (F20%):	0.216
30% Bioavailability (F30%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.981
Plasma Protein Binding (PPB):	91.85118865966797%
Volume Distribution (VD):	1.94
Pgp-substrate:	5.804086685180664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.393
CYP2C19-inhibitor:	0.618
CYP2C19-substrate:	0.762
CYP2C9-inhibitor:	0.745
CYP2C9-substrate:	0.404
CYP2D6-inhibitor:	0.333
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.916
CYP3A4-substrate:	0.841

ADMET: Excretion

Clearance (CL):	3.665
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.447
Human Hepatotoxicity (H-HT):	0.507
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.44
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.899
Carcinogencity:	0.799
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC176840

Natural Product ID:	NPC176840
*Common Name:**	Delta-16-Withanolide
IUPAC Name:	(2R)-2-[(1R)-1-hydroxy-1-[(8R,9S,10R,13R,14R)-14-hydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,15-hexahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	ZIJCEYWPASOHCN-AZEXKZARSA-N
Standard InCHI:	InChI=1S/C28H36O5/c1-16-15-23(33-24(30)17(16)2)27(5,31)21-12-14-28(32)20-10-9-18-7-6-8-22(29)26(18,4)19(20)11-13-25(21,28)3/h6,8-9,12,19-20,23,31-32H,7,10-11,13-15H2,1-5H3/t19-,20+,23+,25+,26-,27+,28+/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@@](C)(C1=CC[C@]2([C@@H]3CC=C4CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333675
PubChem CID:	71718837
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
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[18952419]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23316950]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13927	Withania coagulans	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	5
Others	5

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	10400.0	nM	PMID[464139]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	100.0	%	PMID[464139]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	100.0	%	PMID[464139]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	69.1	%	PMID[464139]
NPT2601	Individual Protein	NF-kappaB inhibitor alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[464140]
NPT2	Others	Unspecified		IC50	=	5700.0	nM	PMID[464139]
NPT2	Others	Unspecified		Inhibition	=	90.2	%	PMID[464139]
NPT2	Others	Unspecified		IC50	=	20800.0	nM	PMID[464140]
NPT2	Others	Unspecified		Imax	=	96.07	%	PMID[464141]
NPT2	Others	Unspecified		IC50	=	38.2	ug.mL-1	PMID[464141]

☑ 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 NPC176840 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	220
0.1-0.2	1229
0.2-0.3	3646
0.3-0.4	6510
0.4-0.5	12898
0.5-0.6	8718
0.6-0.7	6868
0.7-0.8	2417
0.8-0.85	153
0.85-0.9	28
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC190286
0.9455	High Similarity	NPC153440
0.9375	High Similarity	NPC46570
0.9369	High Similarity	NPC5292
0.9292	High Similarity	NPC107493
0.9286	High Similarity	NPC79579
0.9286	High Similarity	NPC474585
0.9196	High Similarity	NPC305260
0.9196	High Similarity	NPC270850
0.9174	High Similarity	NPC236217
0.9027	High Similarity	NPC475041
0.9009	High Similarity	NPC474181
0.8991	High Similarity	NPC37116
0.8909	High Similarity	NPC470961
0.8879	High Similarity	NPC469789
0.8818	High Similarity	NPC473627
0.8818	High Similarity	NPC29133
0.8793	High Similarity	NPC269642
0.8772	High Similarity	NPC186525
0.8761	High Similarity	NPC64318
0.8729	High Similarity	NPC293112
0.8718	High Similarity	NPC473979
0.8707	High Similarity	NPC67569
0.8661	High Similarity	NPC191620
0.8644	High Similarity	NPC172154
0.8644	High Similarity	NPC8369
0.8644	High Similarity	NPC81736
0.8632	High Similarity	NPC170538
0.8632	High Similarity	NPC470265
0.8632	High Similarity	NPC23786
0.8609	High Similarity	NPC475913
0.8584	High Similarity	NPC25909
0.8571	High Similarity	NPC473635
0.8559	High Similarity	NPC11895
0.8534	High Similarity	NPC474179
0.8534	High Similarity	NPC475834
0.8522	High Similarity	NPC470493
0.8522	High Similarity	NPC312824
0.8522	High Similarity	NPC284068
0.8522	High Similarity	NPC183580
0.8519	High Similarity	NPC475320
0.8496	Intermediate Similarity	NPC152117
0.8496	Intermediate Similarity	NPC269530
0.8496	Intermediate Similarity	NPC234042
0.8487	Intermediate Similarity	NPC8374
0.8482	Intermediate Similarity	NPC5103
0.8482	Intermediate Similarity	NPC197428
0.8462	Intermediate Similarity	NPC474370
0.8455	Intermediate Similarity	NPC323834
0.8448	Intermediate Similarity	NPC50774
0.8448	Intermediate Similarity	NPC709
0.843	Intermediate Similarity	NPC245094
0.8421	Intermediate Similarity	NPC250109
0.8421	Intermediate Similarity	NPC469496
0.8421	Intermediate Similarity	NPC471204
0.8421	Intermediate Similarity	NPC962
0.8421	Intermediate Similarity	NPC469463
0.8421	Intermediate Similarity	NPC255017
0.8421	Intermediate Similarity	NPC469454
0.8407	Intermediate Similarity	NPC179798
0.8407	Intermediate Similarity	NPC304180
0.8403	Intermediate Similarity	NPC120724
0.8393	Intermediate Similarity	NPC41405
0.839	Intermediate Similarity	NPC202051
0.8376	Intermediate Similarity	NPC264954
0.8362	Intermediate Similarity	NPC167606
0.8362	Intermediate Similarity	NPC470492
0.8362	Intermediate Similarity	NPC286528
0.8362	Intermediate Similarity	NPC20302
0.8362	Intermediate Similarity	NPC473968
0.8362	Intermediate Similarity	NPC140055
0.8361	Intermediate Similarity	NPC231529
0.8348	Intermediate Similarity	NPC470953
0.8348	Intermediate Similarity	NPC147912
0.8348	Intermediate Similarity	NPC67259
0.8347	Intermediate Similarity	NPC287423
0.8333	Intermediate Similarity	NPC470063
0.8333	Intermediate Similarity	NPC471041
0.8319	Intermediate Similarity	NPC5284
0.8319	Intermediate Similarity	NPC88326
0.8319	Intermediate Similarity	NPC153700
0.8305	Intermediate Similarity	NPC476961
0.8304	Intermediate Similarity	NPC189075
0.8304	Intermediate Similarity	NPC275539
0.8276	Intermediate Similarity	NPC266728
0.8276	Intermediate Similarity	NPC148458
0.8276	Intermediate Similarity	NPC49492
0.8261	Intermediate Similarity	NPC56448
0.8261	Intermediate Similarity	NPC194100
0.825	Intermediate Similarity	NPC204812
0.8246	Intermediate Similarity	NPC324683
0.8246	Intermediate Similarity	NPC188738
0.8235	Intermediate Similarity	NPC310511
0.823	Intermediate Similarity	NPC5475
0.823	Intermediate Similarity	NPC284828
0.823	Intermediate Similarity	NPC173905
0.823	Intermediate Similarity	NPC472216
0.8226	Intermediate Similarity	NPC471855
0.822	Intermediate Similarity	NPC475520
0.822	Intermediate Similarity	NPC61520
0.822	Intermediate Similarity	NPC473203
0.822	Intermediate Similarity	NPC77689
0.822	Intermediate Similarity	NPC476529
0.822	Intermediate Similarity	NPC475775
0.822	Intermediate Similarity	NPC473636
0.8214	Intermediate Similarity	NPC110496
0.8214	Intermediate Similarity	NPC91034
0.8214	Intermediate Similarity	NPC475294
0.8211	Intermediate Similarity	NPC473593
0.8205	Intermediate Similarity	NPC469684
0.8205	Intermediate Similarity	NPC23046
0.8205	Intermediate Similarity	NPC134430
0.8198	Intermediate Similarity	NPC146731
0.8197	Intermediate Similarity	NPC470882
0.8197	Intermediate Similarity	NPC473265
0.8197	Intermediate Similarity	NPC473253
0.8182	Intermediate Similarity	NPC295791
0.8182	Intermediate Similarity	NPC119601
0.8182	Intermediate Similarity	NPC308726
0.8182	Intermediate Similarity	NPC470922
0.8182	Intermediate Similarity	NPC162973
0.8182	Intermediate Similarity	NPC32868
0.8182	Intermediate Similarity	NPC241456
0.8182	Intermediate Similarity	NPC473424
0.8174	Intermediate Similarity	NPC90952
0.8174	Intermediate Similarity	NPC277769
0.8165	Intermediate Similarity	NPC471413
0.8165	Intermediate Similarity	NPC241221
0.8151	Intermediate Similarity	NPC107338
0.8151	Intermediate Similarity	NPC48692
0.8151	Intermediate Similarity	NPC475885
0.8151	Intermediate Similarity	NPC109607
0.8151	Intermediate Similarity	NPC476962
0.8151	Intermediate Similarity	NPC154491
0.8151	Intermediate Similarity	NPC268530
0.8145	Intermediate Similarity	NPC213634
0.8145	Intermediate Similarity	NPC173347
0.8142	Intermediate Similarity	NPC472218
0.8142	Intermediate Similarity	NPC65941
0.8142	Intermediate Similarity	NPC472825
0.8142	Intermediate Similarity	NPC472217
0.8142	Intermediate Similarity	NPC472219
0.8136	Intermediate Similarity	NPC257457
0.8136	Intermediate Similarity	NPC329736
0.8136	Intermediate Similarity	NPC146280
0.8136	Intermediate Similarity	NPC311554
0.8136	Intermediate Similarity	NPC124676
0.813	Intermediate Similarity	NPC311534
0.813	Intermediate Similarity	NPC473888
0.8125	Intermediate Similarity	NPC469607
0.8125	Intermediate Similarity	NPC96377
0.812	Intermediate Similarity	NPC471127
0.812	Intermediate Similarity	NPC270929
0.812	Intermediate Similarity	NPC154363
0.812	Intermediate Similarity	NPC476963
0.812	Intermediate Similarity	NPC234858
0.8108	Intermediate Similarity	NPC264048
0.8108	Intermediate Similarity	NPC99266
0.8108	Intermediate Similarity	NPC254202
0.8108	Intermediate Similarity	NPC236390
0.8103	Intermediate Similarity	NPC472926
0.8103	Intermediate Similarity	NPC122056
0.8103	Intermediate Similarity	NPC317210
0.8091	Intermediate Similarity	NPC476240
0.8091	Intermediate Similarity	NPC476223
0.8091	Intermediate Similarity	NPC472924
0.8091	Intermediate Similarity	NPC471412
0.8091	Intermediate Similarity	NPC224720
0.8091	Intermediate Similarity	NPC310981
0.8091	Intermediate Similarity	NPC163372
0.8091	Intermediate Similarity	NPC302537
0.8087	Intermediate Similarity	NPC471484
0.8087	Intermediate Similarity	NPC475480
0.8087	Intermediate Similarity	NPC262083
0.8087	Intermediate Similarity	NPC470076
0.8087	Intermediate Similarity	NPC473921
0.8087	Intermediate Similarity	NPC475668
0.8083	Intermediate Similarity	NPC159456
0.8083	Intermediate Similarity	NPC204731
0.8083	Intermediate Similarity	NPC4021
0.808	Intermediate Similarity	NPC231240
0.808	Intermediate Similarity	NPC155529
0.8073	Intermediate Similarity	NPC197386
0.8073	Intermediate Similarity	NPC471717
0.807	Intermediate Similarity	NPC273433
0.807	Intermediate Similarity	NPC469370
0.8067	Intermediate Similarity	NPC476960
0.8067	Intermediate Similarity	NPC156745
0.8067	Intermediate Similarity	NPC236918
0.8067	Intermediate Similarity	NPC230513
0.8067	Intermediate Similarity	NPC473839
0.8067	Intermediate Similarity	NPC211093
0.8067	Intermediate Similarity	NPC472667
0.8065	Intermediate Similarity	NPC476966
0.8065	Intermediate Similarity	NPC470880
0.8065	Intermediate Similarity	NPC471407
0.8056	Intermediate Similarity	NPC328371
0.8056	Intermediate Similarity	NPC29952
0.8053	Intermediate Similarity	NPC475060
0.8053	Intermediate Similarity	NPC220229

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 NPC176840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1486
0.2-0.3	3466
0.3-0.4	2454
0.4-0.5	1011
0.5-0.6	295
0.6-0.7	201
0.7-0.8	47
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
0.8362	Intermediate Similarity	NPD7115	Discovery
0.8103	Intermediate Similarity	NPD4632	Approved
0.7863	Intermediate Similarity	NPD8297	Approved
0.7851	Intermediate Similarity	NPD6319	Approved
0.7838	Intermediate Similarity	NPD7640	Approved
0.7838	Intermediate Similarity	NPD7639	Approved
0.7826	Intermediate Similarity	NPD6899	Approved
0.7826	Intermediate Similarity	NPD6881	Approved
0.7823	Intermediate Similarity	NPD7507	Approved
0.775	Intermediate Similarity	NPD6009	Approved
0.7748	Intermediate Similarity	NPD7638	Approved
0.7739	Intermediate Similarity	NPD5697	Approved
0.7712	Intermediate Similarity	NPD6053	Discontinued
0.7692	Intermediate Similarity	NPD7102	Approved
0.7692	Intermediate Similarity	NPD6883	Approved
0.7692	Intermediate Similarity	NPD7290	Approved
0.7672	Intermediate Similarity	NPD6011	Approved
0.7661	Intermediate Similarity	NPD7604	Phase 2
0.7652	Intermediate Similarity	NPD7128	Approved
0.7652	Intermediate Similarity	NPD6008	Approved
0.7652	Intermediate Similarity	NPD6675	Approved
0.7652	Intermediate Similarity	NPD5739	Approved
0.7652	Intermediate Similarity	NPD6402	Approved
0.7642	Intermediate Similarity	NPD5983	Phase 2
0.7642	Intermediate Similarity	NPD7503	Approved
0.7638	Intermediate Similarity	NPD7319	Approved
0.7627	Intermediate Similarity	NPD6617	Approved
0.7627	Intermediate Similarity	NPD6869	Approved
0.7627	Intermediate Similarity	NPD6847	Approved
0.7627	Intermediate Similarity	NPD6649	Approved
0.7627	Intermediate Similarity	NPD6650	Approved
0.7627	Intermediate Similarity	NPD8130	Phase 1
0.7607	Intermediate Similarity	NPD6013	Approved
0.7607	Intermediate Similarity	NPD6012	Approved
0.7607	Intermediate Similarity	NPD6014	Approved
0.76	Intermediate Similarity	NPD7492	Approved
0.7563	Intermediate Similarity	NPD6882	Approved
0.7561	Intermediate Similarity	NPD6054	Approved
0.7559	Intermediate Similarity	NPD7736	Approved
0.7544	Intermediate Similarity	NPD5211	Phase 2
0.7542	Intermediate Similarity	NPD6371	Approved
0.754	Intermediate Similarity	NPD6336	Discontinued
0.754	Intermediate Similarity	NPD6616	Approved
0.7521	Intermediate Similarity	NPD6686	Approved
0.7521	Intermediate Similarity	NPD7320	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.7458	Intermediate Similarity	NPD6373	Approved
0.7458	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6372	Approved
0.744	Intermediate Similarity	NPD6370	Approved
0.7436	Intermediate Similarity	NPD5701	Approved
0.7436	Intermediate Similarity	NPD6412	Phase 2
0.7414	Intermediate Similarity	NPD5141	Approved
0.7395	Intermediate Similarity	NPD4634	Approved
0.7385	Intermediate Similarity	NPD7260	Phase 2
0.7368	Intermediate Similarity	NPD5285	Approved
0.7368	Intermediate Similarity	NPD5286	Approved
0.7368	Intermediate Similarity	NPD4696	Approved
0.7364	Intermediate Similarity	NPD6079	Approved
0.736	Intermediate Similarity	NPD6016	Approved
0.736	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5695	Phase 3
0.7304	Intermediate Similarity	NPD5223	Approved
0.7302	Intermediate Similarity	NPD5988	Approved
0.7297	Intermediate Similarity	NPD6399	Phase 3
0.7281	Intermediate Similarity	NPD4225	Approved
0.728	Intermediate Similarity	NPD6059	Approved
0.7258	Intermediate Similarity	NPD6335	Approved
0.7258	Intermediate Similarity	NPD7327	Approved
0.7258	Intermediate Similarity	NPD7328	Approved
0.725	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5226	Approved
0.7241	Intermediate Similarity	NPD5224	Approved
0.7241	Intermediate Similarity	NPD5225	Approved
0.7241	Intermediate Similarity	NPD4633	Approved
0.7241	Intermediate Similarity	NPD7632	Discontinued
0.7232	Intermediate Similarity	NPD7748	Approved
0.7227	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8513	Phase 3
0.7222	Intermediate Similarity	NPD8033	Approved
0.7209	Intermediate Similarity	NPD8293	Discontinued
0.7207	Intermediate Similarity	NPD5284	Approved
0.7207	Intermediate Similarity	NPD5281	Approved
0.72	Intermediate Similarity	NPD7516	Approved
0.72	Intermediate Similarity	NPD7100	Approved
0.72	Intermediate Similarity	NPD7101	Approved
0.7193	Intermediate Similarity	NPD6084	Phase 2
0.7193	Intermediate Similarity	NPD7902	Approved
0.7193	Intermediate Similarity	NPD4755	Approved
0.7193	Intermediate Similarity	NPD6083	Phase 2
0.7182	Intermediate Similarity	NPD5328	Approved
0.7179	Intermediate Similarity	NPD5174	Approved
0.7179	Intermediate Similarity	NPD5175	Approved
0.7177	Intermediate Similarity	NPD6317	Approved
0.7156	Intermediate Similarity	NPD3573	Approved
0.7155	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD8377	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8294	Approved
0.713	Intermediate Similarity	NPD1694	Approved
0.712	Intermediate Similarity	NPD6313	Approved
0.712	Intermediate Similarity	NPD6314	Approved
0.7105	Intermediate Similarity	NPD5221	Approved
0.7105	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5222	Approved
0.7097	Intermediate Similarity	NPD6274	Approved
0.7091	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8378	Approved
0.7087	Intermediate Similarity	NPD8335	Approved
0.7087	Intermediate Similarity	NPD8516	Approved
0.7087	Intermediate Similarity	NPD8380	Approved
0.7087	Intermediate Similarity	NPD8296	Approved
0.7087	Intermediate Similarity	NPD8517	Approved
0.7087	Intermediate Similarity	NPD8379	Approved
0.7087	Intermediate Similarity	NPD8515	Approved
0.7069	Intermediate Similarity	NPD4700	Approved
0.7064	Intermediate Similarity	NPD6684	Approved
0.7064	Intermediate Similarity	NPD7334	Approved
0.7064	Intermediate Similarity	NPD6409	Approved
0.7064	Intermediate Similarity	NPD7521	Approved
0.7064	Intermediate Similarity	NPD5330	Approved
0.7064	Intermediate Similarity	NPD7146	Approved
0.7054	Intermediate Similarity	NPD5693	Phase 1
0.7054	Intermediate Similarity	NPD7515	Phase 2
0.7043	Intermediate Similarity	NPD5173	Approved
0.7018	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4202	Approved
0.6983	Remote Similarity	NPD5696	Approved
0.6977	Remote Similarity	NPD8328	Phase 3
0.6964	Remote Similarity	NPD6698	Approved
0.6964	Remote Similarity	NPD5785	Approved
0.6964	Remote Similarity	NPD46	Approved
0.696	Remote Similarity	NPD6868	Approved
0.6953	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4729	Approved
0.6942	Remote Similarity	NPD4730	Approved
0.694	Remote Similarity	NPD6845	Suspended
0.6937	Remote Similarity	NPD6672	Approved
0.6937	Remote Similarity	NPD6903	Approved
0.6937	Remote Similarity	NPD5737	Approved
0.6935	Remote Similarity	NPD8133	Approved
0.693	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7900	Approved
0.6923	Remote Similarity	NPD6648	Approved
0.6911	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5690	Phase 2
0.6903	Remote Similarity	NPD6050	Approved
0.6903	Remote Similarity	NPD5694	Approved
0.6903	Remote Similarity	NPD6411	Approved
0.6894	Remote Similarity	NPD6033	Approved
0.6891	Remote Similarity	NPD4754	Approved
0.6885	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6904	Approved
0.6875	Remote Similarity	NPD6673	Approved
0.6875	Remote Similarity	NPD6080	Approved
0.687	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5169	Approved
0.6829	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5251	Approved
0.6829	Remote Similarity	NPD5250	Approved
0.6829	Remote Similarity	NPD5249	Phase 3
0.6829	Remote Similarity	NPD5248	Approved
0.6829	Remote Similarity	NPD5247	Approved
0.6829	Remote Similarity	NPD5135	Approved
0.6822	Remote Similarity	NPD6909	Approved
0.6822	Remote Similarity	NPD6908	Approved
0.6814	Remote Similarity	NPD5207	Approved
0.6814	Remote Similarity	NPD5692	Phase 3
0.681	Remote Similarity	NPD4697	Phase 3
0.6803	Remote Similarity	NPD5128	Approved
0.6777	Remote Similarity	NPD4767	Approved
0.6777	Remote Similarity	NPD4768	Approved
0.6774	Remote Similarity	NPD5215	Approved
0.6774	Remote Similarity	NPD5127	Approved
0.6774	Remote Similarity	NPD5217	Approved
0.6774	Remote Similarity	NPD5216	Approved
0.6757	Remote Similarity	NPD3618	Phase 1
0.6757	Remote Similarity	NPD4623	Approved
0.6757	Remote Similarity	NPD4519	Discontinued
0.6754	Remote Similarity	NPD7983	Approved
0.6754	Remote Similarity	NPD8035	Phase 2
0.6754	Remote Similarity	NPD8034	Phase 2
0.6727	Remote Similarity	NPD3665	Phase 1
0.6727	Remote Similarity	NPD3133	Approved
0.6727	Remote Similarity	NPD3666	Approved
0.6727	Remote Similarity	NPD4786	Approved
0.6726	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6101	Approved
0.6726	Remote Similarity	NPD4753	Phase 2
0.6726	Remote Similarity	NPD6051	Approved
0.6724	Remote Similarity	NPD5210	Approved
0.6724	Remote Similarity	NPD4629	Approved
0.6697	Remote Similarity	NPD4223	Phase 3
0.6697	Remote Similarity	NPD4221	Approved
0.6695	Remote Similarity	NPD8029	Clinical (unspecified phase)

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