NPASS Compound

Structure

NPC190286 OpenBabel07101718202D 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 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 1 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 1 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:	454.27
Volume:	480.831
LogP:	3.426
LogD:	2.618
LogS:	-4.846
# 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:	0.603
Synthetic Accessibility Score:	5.2
Fsp3:	0.714
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:	-4.79
MDCK Permeability:	2.6634999812813476e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.234
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	90.31131744384766%
Volume Distribution (VD):	1.504
Pgp-substrate:	5.168140888214111%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.293
CYP2C19-inhibitor:	0.557
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.594
CYP2C9-substrate:	0.354
CYP2D6-inhibitor:	0.266
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.728

ADMET: Excretion

Clearance (CL):	4.664
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.681
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.579
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.955
Carcinogencity:	0.509
Eye Corrosion:	0.005
Eye Irritation:	0.043
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC190286

Natural Product ID:	NPC190286
*Common Name:**	Withanolide G
IUPAC Name:	(2R)-2-[(1R)-1-hydroxy-1-[(8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,15,16,17-octahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	ZRJOVYPUBHQEES-HZRISEJCSA-N
Standard InCHI:	InChI=1S/C28H38O5/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/h6,8-9,19-21,23,31-32H,7,10-15H2,1-5H3/t19-,20+,21-,23+,25+,26-,27+,28+/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@@](C)([C@H]1CC[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:	CHEMBL2333678
PubChem CID:	21679023
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	4
Others	4

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	37500.0	nM	PMID[475827]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	71.9	%	PMID[475827]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	100.0	%	PMID[475827]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	88.5	%	PMID[475827]
NPT2601	Individual Protein	NF-kappaB inhibitor alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[475828]
NPT2	Others	Unspecified		IC50	=	12300.0	nM	PMID[475827]
NPT2	Others	Unspecified		Inhibition	=	86.9	%	PMID[475827]
NPT2	Others	Unspecified		IC50	=	20700.0	nM	PMID[475828]

☑ 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 NPC190286 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	1236
0.2-0.3	3895
0.3-0.4	7190
0.4-0.5	13108
0.5-0.6	6795
0.6-0.7	7152
0.7-0.8	2792
0.8-0.85	241
0.85-0.9	47
0.9-0.95	10
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC153440
0.9725	High Similarity	NPC5292
0.9636	High Similarity	NPC79579
0.9636	High Similarity	NPC474585
0.963	High Similarity	NPC176840
0.955	High Similarity	NPC46570
0.9545	High Similarity	NPC270850
0.9545	High Similarity	NPC305260
0.9464	High Similarity	NPC107493
0.9196	High Similarity	NPC475041
0.9174	High Similarity	NPC236217
0.9043	High Similarity	NPC473979
0.9009	High Similarity	NPC474181
0.8991	High Similarity	NPC473627
0.8991	High Similarity	NPC37116
0.8957	High Similarity	NPC269642
0.8879	High Similarity	NPC469789
0.8829	High Similarity	NPC191620
0.8818	High Similarity	NPC197428
0.8793	High Similarity	NPC170538
0.8729	High Similarity	NPC473635
0.8729	High Similarity	NPC293112
0.8718	High Similarity	NPC11895
0.8707	High Similarity	NPC67569
0.8692	High Similarity	NPC475320
0.8667	High Similarity	NPC231529
0.8655	High Similarity	NPC287423
0.8644	High Similarity	NPC8374
0.8644	High Similarity	NPC172154
0.8644	High Similarity	NPC8369
0.8644	High Similarity	NPC81736
0.8632	High Similarity	NPC470265
0.8632	High Similarity	NPC23786
0.8621	High Similarity	NPC474370
0.8609	High Similarity	NPC475913
0.8584	High Similarity	NPC250109
0.8584	High Similarity	NPC194100
0.8584	High Similarity	NPC962
0.8583	High Similarity	NPC245094
0.8571	High Similarity	NPC470961
0.8559	High Similarity	NPC120724
0.8559	High Similarity	NPC204812
0.8547	High Similarity	NPC310511
0.8534	High Similarity	NPC474179
0.8534	High Similarity	NPC475834
0.8534	High Similarity	NPC473203
0.8534	High Similarity	NPC264954
0.8525	High Similarity	NPC471855
0.8509	High Similarity	NPC470953
0.8487	Intermediate Similarity	NPC32868
0.8487	Intermediate Similarity	NPC241456
0.8482	Intermediate Similarity	NPC29133
0.8475	Intermediate Similarity	NPC153700
0.8475	Intermediate Similarity	NPC88326
0.8468	Intermediate Similarity	NPC472825
0.8462	Intermediate Similarity	NPC476961
0.8455	Intermediate Similarity	NPC323834
0.8448	Intermediate Similarity	NPC186525
0.8448	Intermediate Similarity	NPC50774
0.8448	Intermediate Similarity	NPC257457
0.8448	Intermediate Similarity	NPC311554
0.8448	Intermediate Similarity	NPC709
0.8443	Intermediate Similarity	NPC213634
0.8443	Intermediate Similarity	NPC173347
0.8435	Intermediate Similarity	NPC266728
0.8435	Intermediate Similarity	NPC64318
0.8435	Intermediate Similarity	NPC49492
0.8435	Intermediate Similarity	NPC148458
0.843	Intermediate Similarity	NPC311534
0.8421	Intermediate Similarity	NPC471204
0.8421	Intermediate Similarity	NPC25909
0.8393	Intermediate Similarity	NPC5475
0.8393	Intermediate Similarity	NPC173905
0.8393	Intermediate Similarity	NPC284828
0.8393	Intermediate Similarity	NPC472216
0.839	Intermediate Similarity	NPC202051
0.8378	Intermediate Similarity	NPC144459
0.8378	Intermediate Similarity	NPC475294
0.8376	Intermediate Similarity	NPC61520
0.8376	Intermediate Similarity	NPC475520
0.8376	Intermediate Similarity	NPC472667
0.8374	Intermediate Similarity	NPC155529
0.8362	Intermediate Similarity	NPC239273
0.8362	Intermediate Similarity	NPC470492
0.8362	Intermediate Similarity	NPC286528
0.8362	Intermediate Similarity	NPC20302
0.8362	Intermediate Similarity	NPC167606
0.8362	Intermediate Similarity	NPC284068
0.8362	Intermediate Similarity	NPC140055
0.8361	Intermediate Similarity	NPC471407
0.8349	Intermediate Similarity	NPC22388
0.8349	Intermediate Similarity	NPC473424
0.8348	Intermediate Similarity	NPC147912
0.8348	Intermediate Similarity	NPC471398
0.8348	Intermediate Similarity	NPC67259
0.8347	Intermediate Similarity	NPC470882
0.8347	Intermediate Similarity	NPC473253
0.8347	Intermediate Similarity	NPC473265
0.8333	Intermediate Similarity	NPC100267
0.8333	Intermediate Similarity	NPC234042
0.8333	Intermediate Similarity	NPC152117
0.8333	Intermediate Similarity	NPC221144
0.8333	Intermediate Similarity	NPC475524
0.8333	Intermediate Similarity	NPC269530
0.832	Intermediate Similarity	NPC158350
0.8319	Intermediate Similarity	NPC5103
0.8304	Intermediate Similarity	NPC65941
0.8304	Intermediate Similarity	NPC275539
0.8304	Intermediate Similarity	NPC189075
0.8291	Intermediate Similarity	NPC475372
0.8291	Intermediate Similarity	NPC329736
0.8288	Intermediate Similarity	NPC231530
0.8288	Intermediate Similarity	NPC96377
0.8288	Intermediate Similarity	NPC278628
0.8279	Intermediate Similarity	NPC473888
0.8276	Intermediate Similarity	NPC476963
0.8276	Intermediate Similarity	NPC196931
0.8273	Intermediate Similarity	NPC236390
0.8273	Intermediate Similarity	NPC474775
0.8264	Intermediate Similarity	NPC159499
0.8261	Intermediate Similarity	NPC469496
0.8261	Intermediate Similarity	NPC317210
0.8261	Intermediate Similarity	NPC255017
0.8261	Intermediate Similarity	NPC469463
0.8261	Intermediate Similarity	NPC469454
0.8257	Intermediate Similarity	NPC310981
0.825	Intermediate Similarity	NPC27363
0.825	Intermediate Similarity	NPC6193
0.8246	Intermediate Similarity	NPC262083
0.8246	Intermediate Similarity	NPC179798
0.8246	Intermediate Similarity	NPC470076
0.8246	Intermediate Similarity	NPC471484
0.8246	Intermediate Similarity	NPC304180
0.8241	Intermediate Similarity	NPC176845
0.8241	Intermediate Similarity	NPC197386
0.823	Intermediate Similarity	NPC41405
0.8224	Intermediate Similarity	NPC42042
0.822	Intermediate Similarity	NPC77689
0.822	Intermediate Similarity	NPC476529
0.822	Intermediate Similarity	NPC475775
0.822	Intermediate Similarity	NPC473636
0.822	Intermediate Similarity	NPC312536
0.822	Intermediate Similarity	NPC476960
0.8214	Intermediate Similarity	NPC220229
0.8214	Intermediate Similarity	NPC110496
0.8214	Intermediate Similarity	NPC475060
0.8214	Intermediate Similarity	NPC91034
0.8211	Intermediate Similarity	NPC470880
0.8211	Intermediate Similarity	NPC221414
0.8211	Intermediate Similarity	NPC473593
0.8211	Intermediate Similarity	NPC476966
0.8205	Intermediate Similarity	NPC471854
0.8205	Intermediate Similarity	NPC470493
0.8205	Intermediate Similarity	NPC473968
0.8205	Intermediate Similarity	NPC183580
0.8205	Intermediate Similarity	NPC476965
0.8205	Intermediate Similarity	NPC312824
0.8205	Intermediate Similarity	NPC476959
0.8205	Intermediate Similarity	NPC470959
0.8205	Intermediate Similarity	NPC134430
0.8198	Intermediate Similarity	NPC96268
0.8198	Intermediate Similarity	NPC255309
0.8198	Intermediate Similarity	NPC28656
0.819	Intermediate Similarity	NPC326542
0.819	Intermediate Similarity	NPC473898
0.819	Intermediate Similarity	NPC178289
0.8182	Intermediate Similarity	NPC119601
0.8182	Intermediate Similarity	NPC308726
0.8182	Intermediate Similarity	NPC473255
0.8182	Intermediate Similarity	NPC195290
0.8182	Intermediate Similarity	NPC162973
0.8182	Intermediate Similarity	NPC204450
0.8182	Intermediate Similarity	NPC469790
0.8174	Intermediate Similarity	NPC470063
0.8174	Intermediate Similarity	NPC126691
0.8174	Intermediate Similarity	NPC207251
0.8174	Intermediate Similarity	NPC277769
0.8174	Intermediate Similarity	NPC71348
0.8167	Intermediate Similarity	NPC222688
0.8165	Intermediate Similarity	NPC471413
0.8165	Intermediate Similarity	NPC241221
0.8158	Intermediate Similarity	NPC41551
0.8158	Intermediate Similarity	NPC76084
0.8158	Intermediate Similarity	NPC5284
0.8158	Intermediate Similarity	NPC16270
0.8151	Intermediate Similarity	NPC268530
0.8151	Intermediate Similarity	NPC107338
0.8151	Intermediate Similarity	NPC41123
0.8151	Intermediate Similarity	NPC109607
0.8151	Intermediate Similarity	NPC109973
0.8151	Intermediate Similarity	NPC476962
0.8151	Intermediate Similarity	NPC154491
0.8151	Intermediate Similarity	NPC251226
0.8151	Intermediate Similarity	NPC143755
0.8151	Intermediate Similarity	NPC145074
0.8151	Intermediate Similarity	NPC114939
0.8148	Intermediate Similarity	NPC18319
0.8142	Intermediate Similarity	NPC472218
0.8142	Intermediate Similarity	NPC177064
0.8142	Intermediate Similarity	NPC472217

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 NPC190286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1450
0.2-0.3	3607
0.3-0.4	2476
0.4-0.5	881
0.5-0.6	259
0.6-0.7	152
0.7-0.8	131
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD4632	Approved
0.8362	Intermediate Similarity	NPD7115	Discovery
0.8174	Intermediate Similarity	NPD8297	Approved
0.8151	Intermediate Similarity	NPD6319	Approved
0.8142	Intermediate Similarity	NPD6899	Approved
0.8142	Intermediate Similarity	NPD6881	Approved
0.8115	Intermediate Similarity	NPD7507	Approved
0.8053	Intermediate Similarity	NPD5697	Approved
0.8051	Intermediate Similarity	NPD6009	Approved
0.8017	Intermediate Similarity	NPD6053	Discontinued
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.7982	Intermediate Similarity	NPD6011	Approved
0.7965	Intermediate Similarity	NPD6402	Approved
0.7965	Intermediate Similarity	NPD7128	Approved
0.7965	Intermediate Similarity	NPD5739	Approved
0.7965	Intermediate Similarity	NPD6008	Approved
0.7965	Intermediate Similarity	NPD6675	Approved
0.7951	Intermediate Similarity	NPD7604	Phase 2
0.7934	Intermediate Similarity	NPD7503	Approved
0.7934	Intermediate Similarity	NPD5983	Phase 2
0.7931	Intermediate Similarity	NPD6649	Approved
0.7931	Intermediate Similarity	NPD6847	Approved
0.7931	Intermediate Similarity	NPD6617	Approved
0.7931	Intermediate Similarity	NPD6650	Approved
0.7931	Intermediate Similarity	NPD6869	Approved
0.7931	Intermediate Similarity	NPD8130	Phase 1
0.792	Intermediate Similarity	NPD7319	Approved
0.7913	Intermediate Similarity	NPD6013	Approved
0.7913	Intermediate Similarity	NPD6014	Approved
0.7913	Intermediate Similarity	NPD6012	Approved
0.7909	Intermediate Similarity	NPD7638	Approved
0.7886	Intermediate Similarity	NPD7492	Approved
0.7863	Intermediate Similarity	NPD6882	Approved
0.7851	Intermediate Similarity	NPD6054	Approved
0.784	Intermediate Similarity	NPD7736	Approved
0.7838	Intermediate Similarity	NPD7640	Approved
0.7838	Intermediate Similarity	NPD7639	Approved
0.7826	Intermediate Similarity	NPD7320	Approved
0.7823	Intermediate Similarity	NPD6336	Discontinued
0.7823	Intermediate Similarity	NPD6616	Approved
0.776	Intermediate Similarity	NPD7078	Approved
0.7759	Intermediate Similarity	NPD6372	Approved
0.7759	Intermediate Similarity	NPD6373	Approved
0.7739	Intermediate Similarity	NPD5701	Approved
0.7739	Intermediate Similarity	NPD6412	Phase 2
0.7724	Intermediate Similarity	NPD6370	Approved
0.7699	Intermediate Similarity	NPD5211	Phase 2
0.7692	Intermediate Similarity	NPD4634	Approved
0.7679	Intermediate Similarity	NPD4696	Approved
0.7679	Intermediate Similarity	NPD5286	Approved
0.7679	Intermediate Similarity	NPD5285	Approved
0.7642	Intermediate Similarity	NPD6015	Approved
0.7642	Intermediate Similarity	NPD6016	Approved
0.7636	Intermediate Similarity	NPD5695	Phase 3
0.7627	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD5223	Approved
0.7581	Intermediate Similarity	NPD5988	Approved
0.7565	Intermediate Similarity	NPD5141	Approved
0.7561	Intermediate Similarity	NPD6059	Approved
0.7544	Intermediate Similarity	NPD4633	Approved
0.7544	Intermediate Similarity	NPD5224	Approved
0.7544	Intermediate Similarity	NPD5226	Approved
0.7544	Intermediate Similarity	NPD5225	Approved
0.7541	Intermediate Similarity	NPD7327	Approved
0.7541	Intermediate Similarity	NPD6335	Approved
0.7541	Intermediate Similarity	NPD7328	Approved
0.7523	Intermediate Similarity	NPD6079	Approved
0.7523	Intermediate Similarity	NPD5281	Approved
0.7523	Intermediate Similarity	NPD5284	Approved
0.7521	Intermediate Similarity	NPD6686	Approved
0.7519	Intermediate Similarity	NPD7260	Phase 2
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.748	Intermediate Similarity	NPD7101	Approved
0.748	Intermediate Similarity	NPD8293	Discontinued
0.748	Intermediate Similarity	NPD7100	Approved
0.748	Intermediate Similarity	NPD7516	Approved
0.7478	Intermediate Similarity	NPD5174	Approved
0.7478	Intermediate Similarity	NPD5175	Approved
0.7459	Intermediate Similarity	NPD6317	Approved
0.7458	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6399	Phase 3
0.7419	Intermediate Similarity	NPD8294	Approved
0.7419	Intermediate Similarity	NPD8377	Approved
0.7407	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6313	Approved
0.7398	Intermediate Similarity	NPD6314	Approved
0.7395	Intermediate Similarity	NPD6371	Approved
0.7383	Intermediate Similarity	NPD6409	Approved
0.7383	Intermediate Similarity	NPD6684	Approved
0.7383	Intermediate Similarity	NPD7334	Approved
0.7383	Intermediate Similarity	NPD7521	Approved
0.7383	Intermediate Similarity	NPD7146	Approved
0.7383	Intermediate Similarity	NPD5330	Approved
0.7377	Intermediate Similarity	NPD6274	Approved
0.7368	Intermediate Similarity	NPD4700	Approved
0.7364	Intermediate Similarity	NPD5693	Phase 1
0.736	Intermediate Similarity	NPD8378	Approved
0.736	Intermediate Similarity	NPD8335	Approved
0.736	Intermediate Similarity	NPD8296	Approved
0.736	Intermediate Similarity	NPD8380	Approved
0.736	Intermediate Similarity	NPD8379	Approved
0.7339	Intermediate Similarity	NPD5328	Approved
0.7321	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4202	Approved
0.7281	Intermediate Similarity	NPD5696	Approved
0.7257	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5221	Approved
0.7257	Intermediate Similarity	NPD5222	Approved
0.725	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6903	Approved
0.7241	Intermediate Similarity	NPD7632	Discontinued
0.7232	Intermediate Similarity	NPD7748	Approved
0.7227	Intermediate Similarity	NPD4730	Approved
0.7227	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4729	Approved
0.7222	Intermediate Similarity	NPD5690	Phase 2
0.7222	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5694	Approved
0.7207	Intermediate Similarity	NPD6050	Approved
0.7193	Intermediate Similarity	NPD5173	Approved
0.7193	Intermediate Similarity	NPD7902	Approved
0.7182	Intermediate Similarity	NPD6673	Approved
0.7182	Intermediate Similarity	NPD6080	Approved
0.7182	Intermediate Similarity	NPD6904	Approved
0.7179	Intermediate Similarity	NPD4754	Approved
0.7156	Intermediate Similarity	NPD3573	Approved
0.7154	Intermediate Similarity	NPD6033	Approved
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD1694	Approved
0.7117	Intermediate Similarity	NPD5785	Approved
0.7117	Intermediate Similarity	NPD5207	Approved
0.7117	Intermediate Similarity	NPD5692	Phase 3
0.7107	Intermediate Similarity	NPD5251	Approved
0.7107	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5247	Approved
0.7107	Intermediate Similarity	NPD5135	Approved
0.7107	Intermediate Similarity	NPD5248	Approved
0.7107	Intermediate Similarity	NPD5249	Phase 3
0.7107	Intermediate Similarity	NPD5250	Approved
0.7107	Intermediate Similarity	NPD5169	Approved
0.7097	Intermediate Similarity	NPD6868	Approved
0.7091	Intermediate Similarity	NPD6672	Approved
0.7091	Intermediate Similarity	NPD5737	Approved
0.7087	Intermediate Similarity	NPD6909	Approved
0.7087	Intermediate Similarity	NPD6908	Approved
0.7087	Intermediate Similarity	NPD8513	Phase 3
0.7083	Intermediate Similarity	NPD5128	Approved
0.7073	Intermediate Similarity	NPD8133	Approved
0.7068	Intermediate Similarity	NPD6845	Suspended
0.7059	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD4767	Approved
0.7054	Intermediate Similarity	NPD7515	Phase 2
0.7049	Intermediate Similarity	NPD5215	Approved
0.7049	Intermediate Similarity	NPD5216	Approved
0.7049	Intermediate Similarity	NPD5217	Approved
0.7049	Intermediate Similarity	NPD5127	Approved
0.7037	Intermediate Similarity	NPD3665	Phase 1
0.7037	Intermediate Similarity	NPD3666	Approved
0.7037	Intermediate Similarity	NPD3133	Approved
0.7027	Intermediate Similarity	NPD4753	Phase 2
0.7027	Intermediate Similarity	NPD6051	Approved
0.7018	Intermediate Similarity	NPD5210	Approved
0.7018	Intermediate Similarity	NPD4629	Approved
0.7009	Intermediate Similarity	NPD4223	Phase 3
0.7009	Intermediate Similarity	NPD4221	Approved
0.7009	Intermediate Similarity	NPD5344	Discontinued
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5778	Approved
0.6991	Remote Similarity	NPD5779	Approved
0.6977	Remote Similarity	NPD8328	Phase 3
0.6972	Remote Similarity	NPD5329	Approved
0.6964	Remote Similarity	NPD6698	Approved
0.6964	Remote Similarity	NPD46	Approved
0.6957	Remote Similarity	NPD4697	Phase 3
0.6953	Remote Similarity	NPD8516	Approved
0.6953	Remote Similarity	NPD8515	Approved
0.6953	Remote Similarity	NPD8517	Approved
0.6937	Remote Similarity	NPD5208	Approved
0.693	Remote Similarity	NPD6001	Approved
0.693	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7900	Approved
0.6909	Remote Similarity	NPD6098	Approved
0.6909	Remote Similarity	NPD5280	Approved
0.6909	Remote Similarity	NPD3618	Phase 1
0.6909	Remote Similarity	NPD4694	Approved
0.6909	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8035	Phase 2
0.6903	Remote Similarity	NPD8034	Phase 2
0.6903	Remote Similarity	NPD6411	Approved
0.6885	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4786	Approved
0.6881	Remote Similarity	NPD4197	Approved
0.688	Remote Similarity	NPD5167	Approved
0.6852	Remote Similarity	NPD4752	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