NPASS Compound

Structure

NPC107493 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 1.5656 -4.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1515 -1.4412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4133 -2.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6783 -0.8551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9464 -3.0899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9464 -2.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1021 -3.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1021 -0.6524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 -0.1649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5689 -2.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7246 -1.6274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3662 0.7888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3966 0.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0437 -3.2122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2890 -5.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8410 -4.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1021 -1.6274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0863 -4.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4133 -1.6274 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4133 -0.6524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2577 -3.0899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3191 -2.5598 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8109 -3.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7246 -0.6524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2577 -2.1149 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7246 -0.6524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5689 -0.1649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4356 -6.0733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4133 -3.5774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7381 -4.1161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3770 0.0722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5386 -0.0630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 0.3013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6081 -2.8611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 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 21 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 11 1 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 22 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 25 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 27 1 1 0 0 0 21 25 1 0 0 0 0 21 30 2 0 0 0 0 22 26 1 1 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 35 1 0 0 0 0 24 27 1 6 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 26 28 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 1 0 0 0 28 24 1 6 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.32
Volume:	588.225
LogP:	4.632
LogD:	2.864
LogS:	-4.928
# Rotatable Bonds:	8
TPSA:	127.18
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	5.418
Fsp3:	0.656
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.785
MDCK Permeability:	1.7340584236080758e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.958
Human Intestinal Absorption (HIA):	0.126
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	94.48265838623047%
Volume Distribution (VD):	3.256
Pgp-substrate:	4.562582015991211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.824

ADMET: Excretion

Clearance (CL):	3.255
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.993
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.137
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.453

Download Data

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

Natural Product: NPC107493

Natural Product ID:	NPC107493
*Common Name:**	(2R)-2-[(1S)-1-[(8R,9S,10R,13S,14R,17S)-14,17-Dihydroxy-10,13-Dimethyl-1-Oxo-4,7,8,9,11,12,15,16-Octahydrocyclopenta[A]Phenanthren-17-Yl]-1-Hydroxyethyl]-5-(Hydroxymethyl)-4-Methyl-2,3-Dihydropyran-6-One
IUPAC Name:	(2R)-2-[(1S)-1-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	NOFNARPLYQSKHE-MEZCUPPISA-N
Standard InCHI:	InChI=1S/C28H38O7/c1-16-14-22(35-23(31)18(16)15-29)26(4,32)28(34)13-12-27(33)20-9-8-17-6-5-7-21(30)25(17,3)19(20)10-11-24(27,28)2/h5,7-8,19-20,22,29,32-34H,6,9-15H2,1-4H3/t19-,20+,22+,24-,25-,26-,27+,28-/m0/s1
SMILES:	CC1=C(CO)C(=O)O[C@H](C1)[C@@](C)([C@@]1(CC[C@]2([C@@H]3CC=C4CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333674
PubChem CID:	71718836
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	2
Others	4

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6900.0	nM	PMID[498523]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	88.6	%	PMID[498523]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	100.0	%	PMID[498523]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	95.1	%	PMID[498523]
NPT2	Others	Unspecified		IC50	=	1600.0	nM	PMID[498523]
NPT2	Others	Unspecified		Inhibition	=	90.1	%	PMID[498523]

☑ 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 NPC107493 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	235
0.1-0.2	1304
0.2-0.3	3950
0.3-0.4	6907
0.4-0.5	12371
0.5-0.6	7784
0.6-0.7	7009
0.7-0.8	2835
0.8-0.85	216
0.85-0.9	57
0.9-0.95	17
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC46570
0.9646	High Similarity	NPC79579
0.9643	High Similarity	NPC153440
0.9558	High Similarity	NPC5292
0.9474	High Similarity	NPC474585
0.9464	High Similarity	NPC190286
0.9386	High Similarity	NPC305260
0.9386	High Similarity	NPC270850
0.9292	High Similarity	NPC176840
0.9231	High Similarity	NPC469789
0.9196	High Similarity	NPC191620
0.9145	High Similarity	NPC269642
0.9076	High Similarity	NPC293112
0.906	High Similarity	NPC67569
0.9052	High Similarity	NPC475041
0.9027	High Similarity	NPC236217
0.8992	High Similarity	NPC8369
0.8992	High Similarity	NPC81736
0.8992	High Similarity	NPC8374
0.8992	High Similarity	NPC172154
0.8983	High Similarity	NPC470265
0.8983	High Similarity	NPC23786
0.8974	High Similarity	NPC474370
0.8938	High Similarity	NPC470961
0.8908	High Similarity	NPC11895
0.8908	High Similarity	NPC473979
0.8889	High Similarity	NPC264954
0.887	High Similarity	NPC474181
0.8852	High Similarity	NPC231529
0.885	High Similarity	NPC37116
0.885	High Similarity	NPC29133
0.8824	High Similarity	NPC88326
0.8824	High Similarity	NPC170538
0.8824	High Similarity	NPC153700
0.8803	High Similarity	NPC50774
0.8803	High Similarity	NPC186525
0.8803	High Similarity	NPC709
0.8793	High Similarity	NPC64318
0.878	High Similarity	NPC173347
0.877	High Similarity	NPC245094
0.876	High Similarity	NPC473635
0.8729	High Similarity	NPC61520
0.8718	High Similarity	NPC470492
0.8718	High Similarity	NPC20302
0.8718	High Similarity	NPC167606
0.8718	High Similarity	NPC140055
0.8718	High Similarity	NPC286528
0.8707	High Similarity	NPC147912
0.8707	High Similarity	NPC67259
0.8707	High Similarity	NPC470953
0.8689	High Similarity	NPC473265
0.8689	High Similarity	NPC287423
0.8689	High Similarity	NPC470882
0.8689	High Similarity	NPC473253
0.8655	High Similarity	NPC476961
0.8644	High Similarity	NPC329736
0.8618	High Similarity	NPC311534
0.8595	High Similarity	NPC204812
0.8584	High Similarity	NPC91034
0.8559	High Similarity	NPC183580
0.8559	High Similarity	NPC239273
0.8559	High Similarity	NPC470493
0.8559	High Similarity	NPC312824
0.8548	High Similarity	NPC221414
0.8548	High Similarity	NPC473593
0.8548	High Similarity	NPC470880
0.8534	High Similarity	NPC269530
0.8525	High Similarity	NPC241456
0.8525	High Similarity	NPC32868
0.8522	High Similarity	NPC197428
0.8522	High Similarity	NPC473627
0.85	High Similarity	NPC476962
0.85	High Similarity	NPC154491
0.85	High Similarity	NPC268530
0.8487	Intermediate Similarity	NPC475913
0.8475	Intermediate Similarity	NPC476963
0.8475	Intermediate Similarity	NPC270929
0.8475	Intermediate Similarity	NPC148458
0.8462	Intermediate Similarity	NPC122056
0.8462	Intermediate Similarity	NPC962
0.8462	Intermediate Similarity	NPC194100
0.8462	Intermediate Similarity	NPC25909
0.8462	Intermediate Similarity	NPC250109
0.8443	Intermediate Similarity	NPC120724
0.843	Intermediate Similarity	NPC4021
0.843	Intermediate Similarity	NPC202051
0.843	Intermediate Similarity	NPC159456
0.843	Intermediate Similarity	NPC473256
0.843	Intermediate Similarity	NPC470878
0.8417	Intermediate Similarity	NPC77689
0.8417	Intermediate Similarity	NPC475520
0.8417	Intermediate Similarity	NPC476960
0.8417	Intermediate Similarity	NPC475834
0.8417	Intermediate Similarity	NPC473203
0.8417	Intermediate Similarity	NPC473636
0.8417	Intermediate Similarity	NPC474179
0.8417	Intermediate Similarity	NPC230513
0.8417	Intermediate Similarity	NPC473270
0.8413	Intermediate Similarity	NPC471855
0.8413	Intermediate Similarity	NPC231240
0.8403	Intermediate Similarity	NPC470959
0.8403	Intermediate Similarity	NPC476959
0.8403	Intermediate Similarity	NPC55296
0.8403	Intermediate Similarity	NPC134430
0.8403	Intermediate Similarity	NPC469684
0.8403	Intermediate Similarity	NPC218970
0.8403	Intermediate Similarity	NPC476965
0.84	Intermediate Similarity	NPC476966
0.839	Intermediate Similarity	NPC326542
0.839	Intermediate Similarity	NPC473898
0.8376	Intermediate Similarity	NPC90952
0.8376	Intermediate Similarity	NPC277769
0.8376	Intermediate Similarity	NPC126691
0.8374	Intermediate Similarity	NPC473255
0.8374	Intermediate Similarity	NPC470922
0.8374	Intermediate Similarity	NPC318135
0.8374	Intermediate Similarity	NPC469790
0.8362	Intermediate Similarity	NPC5103
0.8359	Intermediate Similarity	NPC158350
0.8348	Intermediate Similarity	NPC472825
0.8348	Intermediate Similarity	NPC65941
0.8347	Intermediate Similarity	NPC251226
0.8346	Intermediate Similarity	NPC316915
0.8333	Intermediate Similarity	NPC323834
0.8333	Intermediate Similarity	NPC257457
0.8333	Intermediate Similarity	NPC475372
0.8333	Intermediate Similarity	NPC213634
0.8333	Intermediate Similarity	NPC311554
0.832	Intermediate Similarity	NPC473888
0.832	Intermediate Similarity	NPC473620
0.8319	Intermediate Similarity	NPC266728
0.8319	Intermediate Similarity	NPC49492
0.8319	Intermediate Similarity	NPC470075
0.8308	Intermediate Similarity	NPC75616
0.8306	Intermediate Similarity	NPC159499
0.8305	Intermediate Similarity	NPC469463
0.8305	Intermediate Similarity	NPC469454
0.8305	Intermediate Similarity	NPC469496
0.8305	Intermediate Similarity	NPC472926
0.8305	Intermediate Similarity	NPC317210
0.8304	Intermediate Similarity	NPC472924
0.8293	Intermediate Similarity	NPC55602
0.8291	Intermediate Similarity	NPC474315
0.8291	Intermediate Similarity	NPC324683
0.8281	Intermediate Similarity	NPC471234
0.8279	Intermediate Similarity	NPC310511
0.8279	Intermediate Similarity	NPC129434
0.8276	Intermediate Similarity	NPC5475
0.8276	Intermediate Similarity	NPC472216
0.8276	Intermediate Similarity	NPC173905
0.8276	Intermediate Similarity	NPC284828
0.8268	Intermediate Similarity	NPC155529
0.8264	Intermediate Similarity	NPC312536
0.8264	Intermediate Similarity	NPC42673
0.8264	Intermediate Similarity	NPC472933
0.8264	Intermediate Similarity	NPC473839
0.8264	Intermediate Similarity	NPC473274
0.8264	Intermediate Similarity	NPC211093
0.8261	Intermediate Similarity	NPC144459
0.8261	Intermediate Similarity	NPC472925
0.8254	Intermediate Similarity	NPC471407
0.825	Intermediate Similarity	NPC470171
0.825	Intermediate Similarity	NPC475809
0.825	Intermediate Similarity	NPC473968
0.825	Intermediate Similarity	NPC473656
0.825	Intermediate Similarity	NPC471854
0.8246	Intermediate Similarity	NPC146731
0.8246	Intermediate Similarity	NPC96268
0.8246	Intermediate Similarity	NPC296950
0.824	Intermediate Similarity	NPC117702
0.824	Intermediate Similarity	NPC471357
0.824	Intermediate Similarity	NPC42399
0.824	Intermediate Similarity	NPC469757
0.824	Intermediate Similarity	NPC146456
0.8235	Intermediate Similarity	NPC243354
0.8235	Intermediate Similarity	NPC238667
0.8235	Intermediate Similarity	NPC284915
0.823	Intermediate Similarity	NPC473424
0.823	Intermediate Similarity	NPC475320
0.8226	Intermediate Similarity	NPC3381
0.8226	Intermediate Similarity	NPC470494
0.822	Intermediate Similarity	NPC4573
0.822	Intermediate Similarity	NPC221144
0.822	Intermediate Similarity	NPC152117
0.822	Intermediate Similarity	NPC207251
0.822	Intermediate Similarity	NPC100267
0.822	Intermediate Similarity	NPC475524
0.822	Intermediate Similarity	NPC476163
0.822	Intermediate Similarity	NPC234042
0.8211	Intermediate Similarity	NPC470419
0.8211	Intermediate Similarity	NPC222688
0.8205	Intermediate Similarity	NPC41551
0.8203	Intermediate Similarity	NPC469673
0.8203	Intermediate Similarity	NPC469674
0.8197	Intermediate Similarity	NPC184555
0.8197	Intermediate Similarity	NPC472004
0.819	Intermediate Similarity	NPC472219
0.819	Intermediate Similarity	NPC329417
0.819	Intermediate Similarity	NPC472218
0.819	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 NPC107493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1539
0.2-0.3	3612
0.3-0.4	2395
0.4-0.5	843
0.5-0.6	278
0.6-0.7	176
0.7-0.8	99
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD7115	Discovery
0.8347	Intermediate Similarity	NPD6319	Approved
0.8151	Intermediate Similarity	NPD4632	Approved
0.811	Intermediate Similarity	NPD7319	Approved
0.808	Intermediate Similarity	NPD7492	Approved
0.8067	Intermediate Similarity	NPD8297	Approved
0.8067	Intermediate Similarity	NPD6053	Discontinued
0.8049	Intermediate Similarity	NPD6054	Approved
0.8034	Intermediate Similarity	NPD6899	Approved
0.8034	Intermediate Similarity	NPD6881	Approved
0.8031	Intermediate Similarity	NPD7736	Approved
0.8016	Intermediate Similarity	NPD7507	Approved
0.8016	Intermediate Similarity	NPD6616	Approved
0.7953	Intermediate Similarity	NPD7078	Approved
0.7949	Intermediate Similarity	NPD5697	Approved
0.792	Intermediate Similarity	NPD6370	Approved
0.7899	Intermediate Similarity	NPD6883	Approved
0.7899	Intermediate Similarity	NPD7102	Approved
0.7899	Intermediate Similarity	NPD4634	Approved
0.7899	Intermediate Similarity	NPD7290	Approved
0.7863	Intermediate Similarity	NPD6402	Approved
0.7863	Intermediate Similarity	NPD7128	Approved
0.7863	Intermediate Similarity	NPD5739	Approved
0.7863	Intermediate Similarity	NPD6675	Approved
0.784	Intermediate Similarity	NPD7503	Approved
0.784	Intermediate Similarity	NPD6016	Approved
0.784	Intermediate Similarity	NPD6015	Approved
0.7833	Intermediate Similarity	NPD6649	Approved
0.7833	Intermediate Similarity	NPD6617	Approved
0.7833	Intermediate Similarity	NPD6847	Approved
0.7833	Intermediate Similarity	NPD6650	Approved
0.7833	Intermediate Similarity	NPD6869	Approved
0.7833	Intermediate Similarity	NPD8130	Phase 1
0.7815	Intermediate Similarity	NPD6013	Approved
0.7815	Intermediate Similarity	NPD6014	Approved
0.7815	Intermediate Similarity	NPD6012	Approved
0.7805	Intermediate Similarity	NPD6009	Approved
0.7778	Intermediate Similarity	NPD5988	Approved
0.7769	Intermediate Similarity	NPD6882	Approved
0.776	Intermediate Similarity	NPD6059	Approved
0.7759	Intermediate Similarity	NPD5211	Phase 2
0.775	Intermediate Similarity	NPD6371	Approved
0.7739	Intermediate Similarity	NPD7639	Approved
0.7739	Intermediate Similarity	NPD7640	Approved
0.7731	Intermediate Similarity	NPD7320	Approved
0.7731	Intermediate Similarity	NPD6011	Approved
0.7717	Intermediate Similarity	NPD7604	Phase 2
0.7698	Intermediate Similarity	NPD5983	Phase 2
0.7674	Intermediate Similarity	NPD8293	Discontinued
0.7667	Intermediate Similarity	NPD6373	Approved
0.7667	Intermediate Similarity	NPD6372	Approved
0.7652	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD5701	Approved
0.7647	Intermediate Similarity	NPD6412	Phase 2
0.7627	Intermediate Similarity	NPD5141	Approved
0.7597	Intermediate Similarity	NPD6336	Discontinued
0.7586	Intermediate Similarity	NPD5286	Approved
0.7586	Intermediate Similarity	NPD5285	Approved
0.7586	Intermediate Similarity	NPD4696	Approved
0.7563	Intermediate Similarity	NPD6008	Approved
0.7559	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD4225	Approved
0.746	Intermediate Similarity	NPD7328	Approved
0.746	Intermediate Similarity	NPD7327	Approved
0.7458	Intermediate Similarity	NPD5224	Approved
0.7458	Intermediate Similarity	NPD5225	Approved
0.7458	Intermediate Similarity	NPD5226	Approved
0.7458	Intermediate Similarity	NPD4633	Approved
0.7438	Intermediate Similarity	NPD6686	Approved
0.7438	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD8513	Phase 3
0.7414	Intermediate Similarity	NPD6083	Phase 2
0.7414	Intermediate Similarity	NPD4755	Approved
0.7414	Intermediate Similarity	NPD6084	Phase 2
0.7402	Intermediate Similarity	NPD7100	Approved
0.7402	Intermediate Similarity	NPD7101	Approved
0.7402	Intermediate Similarity	NPD7516	Approved
0.7398	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5175	Approved
0.7395	Intermediate Similarity	NPD5174	Approved
0.7391	Intermediate Similarity	NPD5695	Phase 3
0.7377	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5223	Approved
0.7368	Intermediate Similarity	NPD5779	Approved
0.7368	Intermediate Similarity	NPD5778	Approved
0.7345	Intermediate Similarity	NPD5785	Approved
0.7344	Intermediate Similarity	NPD8377	Approved
0.7344	Intermediate Similarity	NPD8294	Approved
0.7323	Intermediate Similarity	NPD6335	Approved
0.7302	Intermediate Similarity	NPD6274	Approved
0.7288	Intermediate Similarity	NPD4700	Approved
0.7287	Intermediate Similarity	NPD8517	Approved
0.7287	Intermediate Similarity	NPD8378	Approved
0.7287	Intermediate Similarity	NPD8296	Approved
0.7287	Intermediate Similarity	NPD8515	Approved
0.7287	Intermediate Similarity	NPD8379	Approved
0.7287	Intermediate Similarity	NPD8516	Approved
0.7287	Intermediate Similarity	NPD8380	Approved
0.7287	Intermediate Similarity	NPD8335	Approved
0.7281	Intermediate Similarity	NPD6079	Approved
0.7244	Intermediate Similarity	NPD6317	Approved
0.7218	Intermediate Similarity	NPD6033	Approved
0.7213	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6314	Approved
0.7188	Intermediate Similarity	NPD6313	Approved
0.7185	Intermediate Similarity	NPD7260	Phase 2
0.7176	Intermediate Similarity	NPD8328	Phase 3
0.7167	Intermediate Similarity	NPD7632	Discontinued
0.7154	Intermediate Similarity	NPD4729	Approved
0.7154	Intermediate Similarity	NPD4730	Approved
0.713	Intermediate Similarity	NPD5284	Approved
0.713	Intermediate Similarity	NPD6411	Approved
0.713	Intermediate Similarity	NPD5281	Approved
0.7105	Intermediate Similarity	NPD5328	Approved
0.7083	Intermediate Similarity	NPD5344	Discontinued
0.7069	Intermediate Similarity	NPD4202	Approved
0.7069	Intermediate Similarity	NPD6399	Phase 3
0.7059	Intermediate Similarity	NPD5696	Approved
0.704	Intermediate Similarity	NPD5248	Approved
0.704	Intermediate Similarity	NPD5250	Approved
0.704	Intermediate Similarity	NPD5251	Approved
0.704	Intermediate Similarity	NPD5247	Approved
0.704	Intermediate Similarity	NPD5249	Phase 3
0.704	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5221	Approved
0.7034	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5222	Approved
0.7023	Intermediate Similarity	NPD6909	Approved
0.7023	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6908	Approved
0.7018	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5128	Approved
0.7008	Intermediate Similarity	NPD8133	Approved
0.6992	Remote Similarity	NPD4767	Approved
0.6992	Remote Similarity	NPD4768	Approved
0.6991	Remote Similarity	NPD6409	Approved
0.6991	Remote Similarity	NPD7146	Approved
0.6991	Remote Similarity	NPD7334	Approved
0.6991	Remote Similarity	NPD6684	Approved
0.6991	Remote Similarity	NPD7521	Approved
0.6991	Remote Similarity	NPD5330	Approved
0.6984	Remote Similarity	NPD5217	Approved
0.6984	Remote Similarity	NPD5216	Approved
0.6984	Remote Similarity	NPD5215	Approved
0.6983	Remote Similarity	NPD5693	Phase 1
0.6983	Remote Similarity	NPD7983	Approved
0.6983	Remote Similarity	NPD7637	Suspended
0.6975	Remote Similarity	NPD5173	Approved
0.6967	Remote Similarity	NPD4754	Approved
0.6957	Remote Similarity	NPD4753	Phase 2
0.6957	Remote Similarity	NPD6101	Approved
0.6957	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5210	Approved
0.6949	Remote Similarity	NPD4629	Approved
0.6949	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5169	Approved
0.6905	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5135	Approved
0.6903	Remote Similarity	NPD5363	Approved
0.6899	Remote Similarity	NPD6868	Approved
0.6897	Remote Similarity	NPD6698	Approved
0.6897	Remote Similarity	NPD46	Approved
0.6889	Remote Similarity	NPD8074	Phase 3
0.687	Remote Similarity	NPD6903	Approved
0.687	Remote Similarity	NPD4522	Approved
0.6864	Remote Similarity	NPD7748	Approved
0.6861	Remote Similarity	NPD5956	Approved
0.685	Remote Similarity	NPD5127	Approved
0.685	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5690	Phase 2
0.6842	Remote Similarity	NPD5786	Approved
0.6838	Remote Similarity	NPD6050	Approved
0.6838	Remote Similarity	NPD5694	Approved
0.6838	Remote Similarity	NPD7515	Phase 2
0.6833	Remote Similarity	NPD7902	Approved
0.6825	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3665	Phase 1
0.6814	Remote Similarity	NPD3666	Approved
0.6814	Remote Similarity	NPD3133	Approved
0.681	Remote Similarity	NPD6080	Approved
0.681	Remote Similarity	NPD6904	Approved
0.681	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6435	Approved
0.6783	Remote Similarity	NPD3573	Approved
0.6767	Remote Similarity	NPD6921	Approved
0.6763	Remote Similarity	NPD6845	Suspended
0.6761	Remote Similarity	NPD6333	Approved
0.6761	Remote Similarity	NPD6334	Approved
0.6757	Remote Similarity	NPD7236	Approved
0.6754	Remote Similarity	NPD1694	Approved
0.6752	Remote Similarity	NPD5207	Approved
0.6752	Remote Similarity	NPD5692	Phase 3
0.675	Remote Similarity	NPD4697	Phase 3
0.6724	Remote Similarity	NPD6672	Approved
0.6724	Remote Similarity	NPD5737	Approved
0.6721	Remote Similarity	NPD6648	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data