NPASS Compound

Structure

NPC46570 OpenBabel07101718192D 34 38 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 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 -5.1727 -3.0917 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 2.5981 1.5000 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 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 -5.4817 -4.0428 0.0000 O 0 0 0 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 25 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 17 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 17 26 1 0 0 0 0 18 24 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 30 2 0 0 0 0 23 27 1 1 0 0 0 23 34 1 0 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 25 28 1 1 0 0 0 26 3 1 1 0 0 0 27 4 1 6 0 0 0 27 32 1 0 0 0 0 28 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.27
Volume:	489.621
LogP:	2.324
LogD:	1.593
LogS:	-4.527
# Rotatable Bonds:	3
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	5.282
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:	-4.791
MDCK Permeability:	2.605509143904783e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.377
Human Intestinal Absorption (HIA):	0.627
20% Bioavailability (F20%):	0.502
30% Bioavailability (F30%):	0.631

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.945
Plasma Protein Binding (PPB):	82.94287872314453%
Volume Distribution (VD):	0.771
Pgp-substrate:	8.419508934020996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.181
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.736

ADMET: Excretion

Clearance (CL):	3.335
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.33
Human Hepatotoxicity (H-HT):	0.417
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.573
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.96
Carcinogencity:	0.49
Eye Corrosion:	0.004
Eye Irritation:	0.063
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC46570

Natural Product ID:	NPC46570
*Common 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]-5-(Hydroxymethyl)-4-Methyl-2,3-Dihydropyran-6-One
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]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	SZVJDQSFFAIGDR-HZRISEJCSA-N
Standard InCHI:	InChI=1S/C28H38O6/c1-16-14-23(34-24(31)18(16)15-29)27(4,32)21-11-13-28(33)20-9-8-17-6-5-7-22(30)26(17,3)19(20)10-12-25(21,28)2/h5,7-8,19-21,23,29,32-33H,6,9-15H2,1-4H3/t19-,20+,21-,23+,25+,26-,27+,28+/m0/s1
SMILES:	OCC1=C(C)C[C@@H](OC1=O)[C@@]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)C(=O)C=CC2)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333677
PubChem CID:	21679032
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	1
Others	4

Activity Type	# Activity
Cell Line	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	100.0	%	PMID[523548]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	100.0	%	PMID[523548]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	31.4	%	PMID[523548]
NPT2	Others	Unspecified		IC50	=	7000.0	nM	PMID[523548]
NPT2	Others	Unspecified		Inhibition	=	92.8	%	PMID[523548]

☑ 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 NPC46570 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	234
0.1-0.2	1275
0.2-0.3	3883
0.3-0.4	6848
0.4-0.5	12141
0.5-0.6	7944
0.6-0.7	6975
0.7-0.8	3030
0.8-0.85	262
0.85-0.9	74
0.9-0.95	21
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC107493
0.9558	High Similarity	NPC79579
0.9554	High Similarity	NPC153440
0.955	High Similarity	NPC190286
0.9469	High Similarity	NPC5292
0.9386	High Similarity	NPC474585
0.9375	High Similarity	NPC176840
0.931	High Similarity	NPC469789
0.9298	High Similarity	NPC305260
0.9298	High Similarity	NPC270850
0.9279	High Similarity	NPC191620
0.9224	High Similarity	NPC269642
0.9153	High Similarity	NPC293112
0.9138	High Similarity	NPC67569
0.913	High Similarity	NPC475041
0.9107	High Similarity	NPC236217
0.9068	High Similarity	NPC8374
0.9068	High Similarity	NPC8369
0.9068	High Similarity	NPC172154
0.9068	High Similarity	NPC81736
0.906	High Similarity	NPC470265
0.906	High Similarity	NPC23786
0.9052	High Similarity	NPC474370
0.9018	High Similarity	NPC470961
0.8983	High Similarity	NPC11895
0.8983	High Similarity	NPC473979
0.8966	High Similarity	NPC264954
0.8947	High Similarity	NPC474181
0.8929	High Similarity	NPC37116
0.8929	High Similarity	NPC29133
0.8926	High Similarity	NPC231529
0.8898	High Similarity	NPC153700
0.8898	High Similarity	NPC88326
0.8898	High Similarity	NPC170538
0.8879	High Similarity	NPC50774
0.8879	High Similarity	NPC186525
0.8879	High Similarity	NPC709
0.887	High Similarity	NPC64318
0.8843	High Similarity	NPC245094
0.8833	High Similarity	NPC473635
0.8803	High Similarity	NPC61520
0.8793	High Similarity	NPC470492
0.8793	High Similarity	NPC167606
0.8793	High Similarity	NPC286528
0.8793	High Similarity	NPC20302
0.8793	High Similarity	NPC140055
0.8783	High Similarity	NPC67259
0.8783	High Similarity	NPC470953
0.8783	High Similarity	NPC147912
0.876	High Similarity	NPC473265
0.876	High Similarity	NPC287423
0.876	High Similarity	NPC473253
0.876	High Similarity	NPC470882
0.8729	High Similarity	NPC476961
0.8718	High Similarity	NPC329736
0.8699	High Similarity	NPC173347
0.8689	High Similarity	NPC311534
0.8667	High Similarity	NPC204812
0.8661	High Similarity	NPC91034
0.8632	High Similarity	NPC470493
0.8632	High Similarity	NPC239273
0.8632	High Similarity	NPC183580
0.8632	High Similarity	NPC312824
0.8618	High Similarity	NPC470880
0.8618	High Similarity	NPC473593
0.8609	High Similarity	NPC269530
0.8596	High Similarity	NPC197428
0.8596	High Similarity	NPC473627
0.8595	High Similarity	NPC241456
0.8595	High Similarity	NPC32868
0.8571	High Similarity	NPC154491
0.8571	High Similarity	NPC476962
0.8571	High Similarity	NPC268530
0.8559	High Similarity	NPC475913
0.8547	High Similarity	NPC476963
0.8547	High Similarity	NPC270929
0.8547	High Similarity	NPC148458
0.8534	High Similarity	NPC194100
0.8534	High Similarity	NPC25909
0.8534	High Similarity	NPC962
0.8534	High Similarity	NPC250109
0.8534	High Similarity	NPC122056
0.8512	High Similarity	NPC120724
0.85	High Similarity	NPC473256
0.85	High Similarity	NPC202051
0.85	High Similarity	NPC159456
0.85	High Similarity	NPC470878
0.85	High Similarity	NPC4021
0.8487	Intermediate Similarity	NPC77689
0.8487	Intermediate Similarity	NPC475834
0.8487	Intermediate Similarity	NPC473636
0.8487	Intermediate Similarity	NPC230513
0.8487	Intermediate Similarity	NPC473270
0.8487	Intermediate Similarity	NPC474179
0.8487	Intermediate Similarity	NPC476960
0.8487	Intermediate Similarity	NPC475520
0.8487	Intermediate Similarity	NPC473203
0.848	Intermediate Similarity	NPC231240
0.848	Intermediate Similarity	NPC471855
0.8475	Intermediate Similarity	NPC55296
0.8475	Intermediate Similarity	NPC134430
0.8475	Intermediate Similarity	NPC469684
0.8475	Intermediate Similarity	NPC476965
0.8475	Intermediate Similarity	NPC218970
0.8475	Intermediate Similarity	NPC470959
0.8475	Intermediate Similarity	NPC476959
0.8468	Intermediate Similarity	NPC221414
0.8468	Intermediate Similarity	NPC476966
0.8462	Intermediate Similarity	NPC473898
0.8448	Intermediate Similarity	NPC90952
0.8448	Intermediate Similarity	NPC277769
0.8443	Intermediate Similarity	NPC469790
0.8443	Intermediate Similarity	NPC318135
0.8443	Intermediate Similarity	NPC473255
0.8443	Intermediate Similarity	NPC470922
0.8435	Intermediate Similarity	NPC5103
0.8421	Intermediate Similarity	NPC472825
0.8421	Intermediate Similarity	NPC65941
0.8417	Intermediate Similarity	NPC251226
0.8413	Intermediate Similarity	NPC316915
0.8407	Intermediate Similarity	NPC323834
0.8403	Intermediate Similarity	NPC311554
0.8403	Intermediate Similarity	NPC257457
0.8403	Intermediate Similarity	NPC475372
0.84	Intermediate Similarity	NPC213634
0.839	Intermediate Similarity	NPC266728
0.839	Intermediate Similarity	NPC49492
0.839	Intermediate Similarity	NPC470075
0.8387	Intermediate Similarity	NPC473888
0.8387	Intermediate Similarity	NPC473620
0.8378	Intermediate Similarity	NPC472924
0.8376	Intermediate Similarity	NPC469463
0.8376	Intermediate Similarity	NPC469496
0.8376	Intermediate Similarity	NPC469454
0.8376	Intermediate Similarity	NPC472926
0.8376	Intermediate Similarity	NPC317210
0.8362	Intermediate Similarity	NPC474315
0.8362	Intermediate Similarity	NPC324683
0.8361	Intermediate Similarity	NPC55602
0.8348	Intermediate Similarity	NPC173905
0.8348	Intermediate Similarity	NPC284828
0.8348	Intermediate Similarity	NPC472216
0.8348	Intermediate Similarity	NPC5475
0.8347	Intermediate Similarity	NPC129434
0.8347	Intermediate Similarity	NPC310511
0.8346	Intermediate Similarity	NPC471234
0.8333	Intermediate Similarity	NPC155529
0.8333	Intermediate Similarity	NPC211093
0.8333	Intermediate Similarity	NPC144459
0.8333	Intermediate Similarity	NPC473274
0.8333	Intermediate Similarity	NPC472925
0.8333	Intermediate Similarity	NPC472933
0.8333	Intermediate Similarity	NPC473839
0.8333	Intermediate Similarity	NPC42673
0.8333	Intermediate Similarity	NPC312536
0.832	Intermediate Similarity	NPC471407
0.8319	Intermediate Similarity	NPC473968
0.8319	Intermediate Similarity	NPC475809
0.8319	Intermediate Similarity	NPC473656
0.8319	Intermediate Similarity	NPC146731
0.8319	Intermediate Similarity	NPC296950
0.8319	Intermediate Similarity	NPC96268
0.8319	Intermediate Similarity	NPC471854
0.8306	Intermediate Similarity	NPC117702
0.8306	Intermediate Similarity	NPC146456
0.8306	Intermediate Similarity	NPC469757
0.8306	Intermediate Similarity	NPC42399
0.8306	Intermediate Similarity	NPC471357
0.8305	Intermediate Similarity	NPC284915
0.8305	Intermediate Similarity	NPC326542
0.8305	Intermediate Similarity	NPC243354
0.8305	Intermediate Similarity	NPC238667
0.8304	Intermediate Similarity	NPC473424
0.8304	Intermediate Similarity	NPC475320
0.8293	Intermediate Similarity	NPC470494
0.8293	Intermediate Similarity	NPC3381
0.8291	Intermediate Similarity	NPC152117
0.8291	Intermediate Similarity	NPC4573
0.8291	Intermediate Similarity	NPC126691
0.8291	Intermediate Similarity	NPC234042
0.8291	Intermediate Similarity	NPC100267
0.8291	Intermediate Similarity	NPC221144
0.8291	Intermediate Similarity	NPC475524
0.8291	Intermediate Similarity	NPC207251
0.8291	Intermediate Similarity	NPC476163
0.8281	Intermediate Similarity	NPC158350
0.8279	Intermediate Similarity	NPC470419
0.8279	Intermediate Similarity	NPC222688
0.8268	Intermediate Similarity	NPC469674
0.8268	Intermediate Similarity	NPC469673
0.8264	Intermediate Similarity	NPC184555
0.8264	Intermediate Similarity	NPC472004
0.8261	Intermediate Similarity	NPC220155
0.8261	Intermediate Similarity	NPC472218
0.8261	Intermediate Similarity	NPC472217
0.8261	Intermediate Similarity	NPC472219
0.8254	Intermediate Similarity	NPC196921
0.8254	Intermediate Similarity	NPC220757
0.825	Intermediate Similarity	NPC284707
0.825	Intermediate Similarity	NPC473720

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 NPC46570 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	1506
0.2-0.3	3583
0.3-0.4	2436
0.4-0.5	855
0.5-0.6	282
0.6-0.7	169
0.7-0.8	112
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8793	High Similarity	NPD7115	Discovery
0.8417	Intermediate Similarity	NPD6319	Approved
0.822	Intermediate Similarity	NPD4632	Approved
0.8175	Intermediate Similarity	NPD7319	Approved
0.8145	Intermediate Similarity	NPD7492	Approved
0.8136	Intermediate Similarity	NPD8297	Approved
0.8115	Intermediate Similarity	NPD6054	Approved
0.8103	Intermediate Similarity	NPD6899	Approved
0.8103	Intermediate Similarity	NPD6881	Approved
0.8095	Intermediate Similarity	NPD7736	Approved
0.808	Intermediate Similarity	NPD7507	Approved
0.808	Intermediate Similarity	NPD6616	Approved
0.8017	Intermediate Similarity	NPD5697	Approved
0.8016	Intermediate Similarity	NPD7078	Approved
0.7984	Intermediate Similarity	NPD6370	Approved
0.7983	Intermediate Similarity	NPD6053	Discontinued
0.7966	Intermediate Similarity	NPD7102	Approved
0.7966	Intermediate Similarity	NPD4634	Approved
0.7966	Intermediate Similarity	NPD7290	Approved
0.7966	Intermediate Similarity	NPD6883	Approved
0.7931	Intermediate Similarity	NPD5739	Approved
0.7931	Intermediate Similarity	NPD7128	Approved
0.7931	Intermediate Similarity	NPD6675	Approved
0.7931	Intermediate Similarity	NPD6402	Approved
0.7903	Intermediate Similarity	NPD6015	Approved
0.7903	Intermediate Similarity	NPD7503	Approved
0.7903	Intermediate Similarity	NPD6016	Approved
0.7899	Intermediate Similarity	NPD8130	Phase 1
0.7899	Intermediate Similarity	NPD6650	Approved
0.7899	Intermediate Similarity	NPD6847	Approved
0.7899	Intermediate Similarity	NPD6869	Approved
0.7899	Intermediate Similarity	NPD6649	Approved
0.7899	Intermediate Similarity	NPD6617	Approved
0.7881	Intermediate Similarity	NPD6012	Approved
0.7881	Intermediate Similarity	NPD6013	Approved
0.7881	Intermediate Similarity	NPD6014	Approved
0.7869	Intermediate Similarity	NPD6009	Approved
0.784	Intermediate Similarity	NPD5988	Approved
0.7833	Intermediate Similarity	NPD6882	Approved
0.7826	Intermediate Similarity	NPD5211	Phase 2
0.7823	Intermediate Similarity	NPD6059	Approved
0.7815	Intermediate Similarity	NPD6371	Approved
0.7807	Intermediate Similarity	NPD7640	Approved
0.7807	Intermediate Similarity	NPD7639	Approved
0.7797	Intermediate Similarity	NPD7320	Approved
0.7797	Intermediate Similarity	NPD6011	Approved
0.7778	Intermediate Similarity	NPD7604	Phase 2
0.776	Intermediate Similarity	NPD5983	Phase 2
0.7734	Intermediate Similarity	NPD8293	Discontinued
0.7731	Intermediate Similarity	NPD6372	Approved
0.7731	Intermediate Similarity	NPD6373	Approved
0.7719	Intermediate Similarity	NPD7638	Approved
0.7712	Intermediate Similarity	NPD6412	Phase 2
0.7712	Intermediate Similarity	NPD5701	Approved
0.7692	Intermediate Similarity	NPD5141	Approved
0.7656	Intermediate Similarity	NPD6336	Discontinued
0.7652	Intermediate Similarity	NPD5285	Approved
0.7652	Intermediate Similarity	NPD5286	Approved
0.7652	Intermediate Similarity	NPD4696	Approved
0.7627	Intermediate Similarity	NPD6008	Approved
0.7565	Intermediate Similarity	NPD4225	Approved
0.7521	Intermediate Similarity	NPD5224	Approved
0.7521	Intermediate Similarity	NPD5225	Approved
0.7521	Intermediate Similarity	NPD5226	Approved
0.7521	Intermediate Similarity	NPD4633	Approved
0.752	Intermediate Similarity	NPD7327	Approved
0.752	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6686	Approved
0.748	Intermediate Similarity	NPD8033	Approved
0.748	Intermediate Similarity	NPD8513	Phase 3
0.7478	Intermediate Similarity	NPD4755	Approved
0.7478	Intermediate Similarity	NPD6084	Phase 2
0.7478	Intermediate Similarity	NPD6083	Phase 2
0.746	Intermediate Similarity	NPD7101	Approved
0.746	Intermediate Similarity	NPD7100	Approved
0.746	Intermediate Similarity	NPD7516	Approved
0.7459	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5175	Approved
0.7458	Intermediate Similarity	NPD5174	Approved
0.7456	Intermediate Similarity	NPD5695	Phase 3
0.7438	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5223	Approved
0.7434	Intermediate Similarity	NPD5779	Approved
0.7434	Intermediate Similarity	NPD5778	Approved
0.7411	Intermediate Similarity	NPD5785	Approved
0.7402	Intermediate Similarity	NPD8294	Approved
0.7402	Intermediate Similarity	NPD8377	Approved
0.7381	Intermediate Similarity	NPD6335	Approved
0.736	Intermediate Similarity	NPD6274	Approved
0.735	Intermediate Similarity	NPD4700	Approved
0.7345	Intermediate Similarity	NPD6079	Approved
0.7344	Intermediate Similarity	NPD8378	Approved
0.7344	Intermediate Similarity	NPD8296	Approved
0.7344	Intermediate Similarity	NPD8515	Approved
0.7344	Intermediate Similarity	NPD8516	Approved
0.7344	Intermediate Similarity	NPD8380	Approved
0.7344	Intermediate Similarity	NPD8517	Approved
0.7344	Intermediate Similarity	NPD8335	Approved
0.7344	Intermediate Similarity	NPD8379	Approved
0.7302	Intermediate Similarity	NPD6317	Approved
0.7273	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6033	Approved
0.7244	Intermediate Similarity	NPD6313	Approved
0.7244	Intermediate Similarity	NPD6314	Approved
0.7239	Intermediate Similarity	NPD7260	Phase 2
0.7231	Intermediate Similarity	NPD8328	Phase 3
0.7227	Intermediate Similarity	NPD7632	Discontinued
0.7213	Intermediate Similarity	NPD4730	Approved
0.7213	Intermediate Similarity	NPD4729	Approved
0.7193	Intermediate Similarity	NPD6411	Approved
0.7193	Intermediate Similarity	NPD5281	Approved
0.7193	Intermediate Similarity	NPD5284	Approved
0.7168	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD5344	Discontinued
0.713	Intermediate Similarity	NPD4202	Approved
0.713	Intermediate Similarity	NPD6399	Phase 3
0.7119	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD5248	Approved
0.7097	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5247	Approved
0.7097	Intermediate Similarity	NPD5250	Approved
0.7097	Intermediate Similarity	NPD5251	Approved
0.7097	Intermediate Similarity	NPD5249	Phase 3
0.7094	Intermediate Similarity	NPD5222	Approved
0.7094	Intermediate Similarity	NPD5221	Approved
0.7094	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6908	Approved
0.7077	Intermediate Similarity	NPD6909	Approved
0.7073	Intermediate Similarity	NPD5128	Approved
0.7063	Intermediate Similarity	NPD8133	Approved
0.7054	Intermediate Similarity	NPD7146	Approved
0.7054	Intermediate Similarity	NPD7521	Approved
0.7054	Intermediate Similarity	NPD7334	Approved
0.7054	Intermediate Similarity	NPD5330	Approved
0.7054	Intermediate Similarity	NPD6684	Approved
0.7054	Intermediate Similarity	NPD6409	Approved
0.7049	Intermediate Similarity	NPD4768	Approved
0.7049	Intermediate Similarity	NPD4767	Approved
0.7043	Intermediate Similarity	NPD7983	Approved
0.7043	Intermediate Similarity	NPD5693	Phase 1
0.7043	Intermediate Similarity	NPD7637	Suspended
0.704	Intermediate Similarity	NPD5215	Approved
0.704	Intermediate Similarity	NPD5216	Approved
0.704	Intermediate Similarity	NPD5217	Approved
0.7034	Intermediate Similarity	NPD5173	Approved
0.7025	Intermediate Similarity	NPD4754	Approved
0.7018	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4753	Phase 2
0.7018	Intermediate Similarity	NPD6101	Approved
0.7009	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5210	Approved
0.7009	Intermediate Similarity	NPD4629	Approved
0.6964	Remote Similarity	NPD5363	Approved
0.696	Remote Similarity	NPD5169	Approved
0.696	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5135	Approved
0.6957	Remote Similarity	NPD6698	Approved
0.6957	Remote Similarity	NPD46	Approved
0.6953	Remote Similarity	NPD6868	Approved
0.694	Remote Similarity	NPD8074	Phase 3
0.693	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD4522	Approved
0.6912	Remote Similarity	NPD5956	Approved
0.6905	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5127	Approved
0.6903	Remote Similarity	NPD5690	Phase 2
0.6903	Remote Similarity	NPD5786	Approved
0.6903	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6050	Approved
0.6897	Remote Similarity	NPD7515	Phase 2
0.6897	Remote Similarity	NPD5694	Approved
0.6891	Remote Similarity	NPD7902	Approved
0.688	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3666	Approved
0.6875	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD3665	Phase 1
0.687	Remote Similarity	NPD6080	Approved
0.687	Remote Similarity	NPD6904	Approved
0.687	Remote Similarity	NPD6673	Approved
0.6855	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3573	Approved
0.6818	Remote Similarity	NPD6921	Approved
0.6814	Remote Similarity	NPD1694	Approved
0.6812	Remote Similarity	NPD6845	Suspended
0.681	Remote Similarity	NPD5207	Approved
0.681	Remote Similarity	NPD5692	Phase 3
0.6809	Remote Similarity	NPD6334	Approved
0.6809	Remote Similarity	NPD6333	Approved
0.6807	Remote Similarity	NPD4697	Phase 3
0.6803	Remote Similarity	NPD7236	Approved
0.6783	Remote Similarity	NPD6672	Approved
0.6783	Remote Similarity	NPD5737	Approved
0.6777	Remote Similarity	NPD6648	Approved
0.6754	Remote Similarity	NPD3618	Phase 1

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