NPASS Compound

Structure

NPC158350 OpenBabel07101719252D 44 49 0 0 1 0 0 0 0 0999 V2000 -0.2024 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 -0.7044 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2346 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 3.0000 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 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 0.0388 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 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5436 0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 -3.6808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5218 0.6625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 1.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 30 1 0 0 0 0 3 6 2 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 4 18 1 0 0 0 0 5 21 1 0 0 0 0 6 24 1 0 0 0 0 7 10 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 30 1 0 0 0 0 10 31 1 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 17 2 0 0 0 0 14 41 1 0 0 0 0 15 34 2 0 0 0 0 16 35 2 0 0 0 0 16 42 1 0 0 0 0 17 25 1 0 0 0 0 18 31 1 0 0 0 0 19 43 1 6 0 0 0 20 21 1 0 0 0 0 20 31 1 6 0 0 0 21 32 1 1 0 0 0 22 25 1 0 0 0 0 22 42 1 1 0 0 0 23 13 1 6 0 0 0 23 26 1 0 0 0 0 23 44 1 0 0 0 0 24 36 2 0 0 0 0 24 41 1 0 0 0 0 25 30 1 6 0 0 0 26 27 1 0 0 0 0 26 37 1 1 0 0 0 27 28 1 0 0 0 0 27 38 1 6 0 0 0 28 29 1 0 0 0 0 28 39 1 1 0 0 0 29 43 1 6 0 0 0 29 44 1 0 0 0 0 30 32 1 6 0 0 0 31 15 1 6 0 0 0 32 40 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.27
Volume:	600.353
LogP:	0.594
LogD:	0.097
LogS:	-2.899
# Rotatable Bonds:	7
TPSA:	193.19
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	5.478
Fsp3:	0.719
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.35
MDCK Permeability:	7.291130896192044e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	57.00159454345703%
Volume Distribution (VD):	0.842
Pgp-substrate:	20.07270622253418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.378
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	1.639
Half-life (T1/2):	0.59

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.136
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.132
Carcinogencity:	0.798
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC158350

Natural Product ID:	NPC158350
*Common Name:**	14Beta-Hydroxy-19Beta-Oxobufa-4,20,22-Trienolide-16Alpha-O-Acetyl-3Beta-O-Beta-D-Glucopyranoside
IUPAC Name:	[(3S,8R,9S,10S,13R,14S,16R,17R)-10-formyl-14-hydroxy-13-methyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-16-yl] acetate
Synonyms:
Standard InCHIKey:	JTVAVGRVPCYJKO-KKCVIFLDSA-N
Standard InCHI:	InChI=1S/C32H42O12/c1-16(35)42-22-12-32(40)21-5-4-18-11-19(43-29-28(39)27(38)26(37)23(13-33)44-29)7-10-31(18,15-34)20(21)8-9-30(32,2)25(22)17-3-6-24(36)41-14-17/h3,6,11,14-15,19-23,25-29,33,37-40H,4-5,7-10,12-13H2,1-2H3/t19-,20-,21+,22+,23+,25-,26+,27-,28+,29+,30+,31+,32-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)C[C@H]([C@@H]3c2ccc(=O)oc2)OC(=O)C)C)C=O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375661
PubChem CID:	71713110
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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
NPO27354	Urginea depressa	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23659371]
NPO27354	Urginea depressa	Species	Hyacinthaceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	11.0	nM	PMID[506143]
NPT1383	Cell Line	A2058	Homo sapiens	IC50	=	60.0	nM	PMID[506143]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44.0	nM	PMID[506143]

☑ 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 NPC158350 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	390
0.1-0.2	1463
0.2-0.3	2892
0.3-0.4	5545
0.4-0.5	10047
0.5-0.6	9947
0.6-0.7	9183
0.7-0.8	2932
0.8-0.85	221
0.85-0.9	43
0.9-0.95	31
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC155529
0.9603	High Similarity	NPC127656
0.9453	High Similarity	NPC75616
0.9297	High Similarity	NPC62172
0.9297	High Similarity	NPC289700
0.9055	High Similarity	NPC173347
0.8889	High Similarity	NPC179261
0.8837	High Similarity	NPC471855
0.8828	High Similarity	NPC329986
0.8828	High Similarity	NPC125077
0.8828	High Similarity	NPC140092
0.8828	High Similarity	NPC276838
0.8828	High Similarity	NPC188234
0.8828	High Similarity	NPC232785
0.8769	High Similarity	NPC225385
0.8769	High Similarity	NPC298783
0.8769	High Similarity	NPC104585
0.8769	High Similarity	NPC157817
0.8769	High Similarity	NPC142756
0.876	High Similarity	NPC213634
0.875	High Similarity	NPC245094
0.874	High Similarity	NPC250556
0.874	High Similarity	NPC469750
0.8702	High Similarity	NPC248703
0.8682	High Similarity	NPC471407
0.8682	High Similarity	NPC476966
0.8672	High Similarity	NPC471356
0.8672	High Similarity	NPC179412
0.8672	High Similarity	NPC329784
0.8672	High Similarity	NPC240070
0.8626	High Similarity	NPC116075
0.8626	High Similarity	NPC469749
0.8626	High Similarity	NPC146857
0.8626	High Similarity	NPC32793
0.8626	High Similarity	NPC477709
0.8626	High Similarity	NPC476221
0.8626	High Similarity	NPC247190
0.8615	High Similarity	NPC16569
0.8615	High Similarity	NPC159338
0.8615	High Similarity	NPC253456
0.8605	High Similarity	NPC311534
0.8594	High Similarity	NPC159499
0.8583	High Similarity	NPC27363
0.8583	High Similarity	NPC219804
0.8561	High Similarity	NPC329636
0.856	High Similarity	NPC270850
0.856	High Similarity	NPC305260
0.856	High Similarity	NPC219656
0.856	High Similarity	NPC5292
0.855	High Similarity	NPC231240
0.855	High Similarity	NPC19124
0.855	High Similarity	NPC93416
0.855	High Similarity	NPC42670
0.8538	High Similarity	NPC471361
0.8538	High Similarity	NPC471360
0.8538	High Similarity	NPC197707
0.8538	High Similarity	NPC469751
0.8538	High Similarity	NPC469752
0.8538	High Similarity	NPC284406
0.8538	High Similarity	NPC471359
0.8538	High Similarity	NPC9499
0.8538	High Similarity	NPC10823
0.8538	High Similarity	NPC251866
0.8538	High Similarity	NPC86159
0.8538	High Similarity	NPC180079
0.8538	High Similarity	NPC70542
0.8538	High Similarity	NPC219085
0.8538	High Similarity	NPC471352
0.8538	High Similarity	NPC17896
0.8538	High Similarity	NPC469754
0.8538	High Similarity	NPC469755
0.8538	High Similarity	NPC469753
0.8538	High Similarity	NPC91
0.8538	High Similarity	NPC6108
0.8538	High Similarity	NPC471358
0.8538	High Similarity	NPC89514
0.8516	High Similarity	NPC318135
0.8496	Intermediate Similarity	NPC194716
0.8492	Intermediate Similarity	NPC79579
0.8485	Intermediate Similarity	NPC316915
0.848	Intermediate Similarity	NPC473617
0.848	Intermediate Similarity	NPC153440
0.848	Intermediate Similarity	NPC45475
0.848	Intermediate Similarity	NPC473828
0.8444	Intermediate Similarity	NPC79250
0.8444	Intermediate Similarity	NPC290746
0.8438	Intermediate Similarity	NPC41129
0.8438	Intermediate Similarity	NPC55602
0.8438	Intermediate Similarity	NPC6193
0.8433	Intermediate Similarity	NPC59288
0.8433	Intermediate Similarity	NPC329675
0.8425	Intermediate Similarity	NPC233500
0.8425	Intermediate Similarity	NPC202051
0.8385	Intermediate Similarity	NPC146456
0.8385	Intermediate Similarity	NPC469757
0.8385	Intermediate Similarity	NPC471357
0.8385	Intermediate Similarity	NPC152091
0.8385	Intermediate Similarity	NPC117702
0.8359	Intermediate Similarity	NPC107493
0.8359	Intermediate Similarity	NPC28532
0.8359	Intermediate Similarity	NPC196130
0.8346	Intermediate Similarity	NPC107607
0.8346	Intermediate Similarity	NPC41123
0.8346	Intermediate Similarity	NPC145074
0.8346	Intermediate Similarity	NPC470312
0.8346	Intermediate Similarity	NPC114939
0.8346	Intermediate Similarity	NPC474585
0.8321	Intermediate Similarity	NPC473888
0.832	Intermediate Similarity	NPC207637
0.832	Intermediate Similarity	NPC190286
0.8281	Intermediate Similarity	NPC46570
0.8281	Intermediate Similarity	NPC476204
0.8281	Intermediate Similarity	NPC475219
0.8281	Intermediate Similarity	NPC231518
0.8281	Intermediate Similarity	NPC170084
0.8268	Intermediate Similarity	NPC477071
0.8268	Intermediate Similarity	NPC29639
0.8268	Intermediate Similarity	NPC5883
0.8268	Intermediate Similarity	NPC304260
0.8268	Intermediate Similarity	NPC81222
0.8268	Intermediate Similarity	NPC291820
0.8268	Intermediate Similarity	NPC44899
0.8258	Intermediate Similarity	NPC221414
0.8254	Intermediate Similarity	NPC203862
0.8244	Intermediate Similarity	NPC42399
0.824	Intermediate Similarity	NPC475163
0.824	Intermediate Similarity	NPC74727
0.8231	Intermediate Similarity	NPC32868
0.8231	Intermediate Similarity	NPC241456
0.8217	Intermediate Similarity	NPC193893
0.8203	Intermediate Similarity	NPC48692
0.8203	Intermediate Similarity	NPC184555
0.8189	Intermediate Similarity	NPC218093
0.8189	Intermediate Similarity	NPC291564
0.8182	Intermediate Similarity	NPC473620
0.8182	Intermediate Similarity	NPC69273
0.8182	Intermediate Similarity	NPC168899
0.8182	Intermediate Similarity	NPC293623
0.8168	Intermediate Similarity	NPC47113
0.8168	Intermediate Similarity	NPC174367
0.8168	Intermediate Similarity	NPC93368
0.816	Intermediate Similarity	NPC260665
0.816	Intermediate Similarity	NPC73050
0.8154	Intermediate Similarity	NPC204812
0.814	Intermediate Similarity	NPC129434
0.814	Intermediate Similarity	NPC42675
0.814	Intermediate Similarity	NPC40749
0.8129	Intermediate Similarity	NPC5153
0.8129	Intermediate Similarity	NPC48414
0.8125	Intermediate Similarity	NPC470897
0.8125	Intermediate Similarity	NPC30483
0.8125	Intermediate Similarity	NPC475041
0.8125	Intermediate Similarity	NPC292467
0.8125	Intermediate Similarity	NPC469756
0.8125	Intermediate Similarity	NPC278681
0.8125	Intermediate Similarity	NPC55532
0.8125	Intermediate Similarity	NPC232258
0.8125	Intermediate Similarity	NPC236973
0.8125	Intermediate Similarity	NPC122971
0.8125	Intermediate Similarity	NPC32177
0.812	Intermediate Similarity	NPC473593
0.811	Intermediate Similarity	NPC93883
0.811	Intermediate Similarity	NPC473968
0.8106	Intermediate Similarity	NPC287423
0.8102	Intermediate Similarity	NPC596
0.8095	Intermediate Similarity	NPC473882
0.8095	Intermediate Similarity	NPC220293
0.8092	Intermediate Similarity	NPC190846
0.8092	Intermediate Similarity	NPC3381
0.8092	Intermediate Similarity	NPC475194
0.8092	Intermediate Similarity	NPC277191
0.8088	Intermediate Similarity	NPC171619
0.8077	Intermediate Similarity	NPC269642
0.8077	Intermediate Similarity	NPC475431
0.8077	Intermediate Similarity	NPC471082
0.8074	Intermediate Similarity	NPC88668
0.8065	Intermediate Similarity	NPC83005
0.8062	Intermediate Similarity	NPC72260
0.8062	Intermediate Similarity	NPC476150
0.8062	Intermediate Similarity	NPC476127
0.8062	Intermediate Similarity	NPC135369
0.8062	Intermediate Similarity	NPC471406
0.8062	Intermediate Similarity	NPC112936
0.8062	Intermediate Similarity	NPC475556
0.8062	Intermediate Similarity	NPC257610
0.8062	Intermediate Similarity	NPC475629
0.806	Intermediate Similarity	NPC241008
0.8047	Intermediate Similarity	NPC472080
0.8047	Intermediate Similarity	NPC471249
0.8047	Intermediate Similarity	NPC13710
0.8047	Intermediate Similarity	NPC16701
0.8045	Intermediate Similarity	NPC114306
0.8045	Intermediate Similarity	NPC477490
0.8045	Intermediate Similarity	NPC220838
0.8045	Intermediate Similarity	NPC45606
0.8031	Intermediate Similarity	NPC310341
0.8031	Intermediate Similarity	NPC99620
0.8031	Intermediate Similarity	NPC193382
0.8031	Intermediate Similarity	NPC199428
0.8031	Intermediate Similarity	NPC5311

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 NPC158350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	867
0.2-0.3	1779
0.3-0.4	2719
0.4-0.5	2126
0.5-0.6	983
0.6-0.7	299
0.7-0.8	41
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD7503	Approved
0.874	High Similarity	NPD7507	Approved
0.8538	High Similarity	NPD7319	Approved
0.8281	Intermediate Similarity	NPD8033	Approved
0.8062	Intermediate Similarity	NPD8294	Approved
0.8062	Intermediate Similarity	NPD8377	Approved
0.8	Intermediate Similarity	NPD8296	Approved
0.8	Intermediate Similarity	NPD8378	Approved
0.8	Intermediate Similarity	NPD8335	Approved
0.8	Intermediate Similarity	NPD8380	Approved
0.8	Intermediate Similarity	NPD8379	Approved
0.791	Intermediate Similarity	NPD7736	Approved
0.7907	Intermediate Similarity	NPD7328	Approved
0.7907	Intermediate Similarity	NPD7327	Approved
0.7903	Intermediate Similarity	NPD6686	Approved
0.7863	Intermediate Similarity	NPD8513	Phase 3
0.7846	Intermediate Similarity	NPD7516	Approved
0.7823	Intermediate Similarity	NPD6412	Phase 2
0.7734	Intermediate Similarity	NPD8133	Approved
0.7727	Intermediate Similarity	NPD8516	Approved
0.7727	Intermediate Similarity	NPD8515	Approved
0.7727	Intermediate Similarity	NPD8517	Approved
0.7669	Intermediate Similarity	NPD6370	Approved
0.7656	Intermediate Similarity	NPD6053	Discontinued
0.7656	Intermediate Similarity	NPD8297	Approved
0.7656	Intermediate Similarity	NPD6882	Approved
0.7574	Intermediate Similarity	NPD8293	Discontinued
0.7557	Intermediate Similarity	NPD6009	Approved
0.7557	Intermediate Similarity	NPD7115	Discovery
0.7556	Intermediate Similarity	NPD7492	Approved
0.7519	Intermediate Similarity	NPD6054	Approved
0.7519	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.7481	Intermediate Similarity	NPD8328	Phase 3
0.7462	Intermediate Similarity	NPD4632	Approved
0.7445	Intermediate Similarity	NPD7078	Approved
0.7344	Intermediate Similarity	NPD6899	Approved
0.7344	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD6016	Approved
0.7308	Intermediate Similarity	NPD6649	Approved
0.7308	Intermediate Similarity	NPD6650	Approved
0.7308	Intermediate Similarity	NPD8130	Phase 1
0.7293	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5988	Approved
0.7266	Intermediate Similarity	NPD5697	Approved
0.7259	Intermediate Similarity	NPD6059	Approved
0.7231	Intermediate Similarity	NPD7102	Approved
0.7231	Intermediate Similarity	NPD6883	Approved
0.7231	Intermediate Similarity	NPD7290	Approved
0.7188	Intermediate Similarity	NPD7128	Approved
0.7188	Intermediate Similarity	NPD6675	Approved
0.7188	Intermediate Similarity	NPD6402	Approved
0.7188	Intermediate Similarity	NPD5739	Approved
0.7176	Intermediate Similarity	NPD6869	Approved
0.7176	Intermediate Similarity	NPD6847	Approved
0.7176	Intermediate Similarity	NPD6617	Approved
0.7154	Intermediate Similarity	NPD6012	Approved
0.7154	Intermediate Similarity	NPD6013	Approved
0.7154	Intermediate Similarity	NPD6373	Approved
0.7154	Intermediate Similarity	NPD6014	Approved
0.7154	Intermediate Similarity	NPD6372	Approved
0.712	Intermediate Similarity	NPD7638	Approved
0.7101	Intermediate Similarity	NPD7604	Phase 2
0.708	Intermediate Similarity	NPD5983	Phase 2
0.7077	Intermediate Similarity	NPD7320	Approved
0.7077	Intermediate Similarity	NPD6011	Approved
0.7063	Intermediate Similarity	NPD7640	Approved
0.7063	Intermediate Similarity	NPD7639	Approved
0.7045	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD6336	Discontinued
0.6993	Remote Similarity	NPD7260	Phase 2
0.697	Remote Similarity	NPD4634	Approved
0.6953	Remote Similarity	NPD5211	Phase 2
0.695	Remote Similarity	NPD8074	Phase 3
0.6929	Remote Similarity	NPD5285	Approved
0.6929	Remote Similarity	NPD4696	Approved
0.6929	Remote Similarity	NPD5286	Approved
0.6923	Remote Similarity	NPD6008	Approved
0.6894	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7799	Discontinued
0.685	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5141	Approved
0.6846	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5225	Approved
0.6822	Remote Similarity	NPD5224	Approved
0.6822	Remote Similarity	NPD4633	Approved
0.6822	Remote Similarity	NPD5226	Approved
0.6812	Remote Similarity	NPD7101	Approved
0.6812	Remote Similarity	NPD7100	Approved
0.6791	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6033	Approved
0.6772	Remote Similarity	NPD6083	Phase 2
0.6772	Remote Similarity	NPD4755	Approved
0.6772	Remote Similarity	NPD6084	Phase 2
0.6769	Remote Similarity	NPD5174	Approved
0.6769	Remote Similarity	NPD5175	Approved
0.6744	Remote Similarity	NPD5223	Approved
0.6739	Remote Similarity	NPD6335	Approved
0.6738	Remote Similarity	NPD6067	Discontinued
0.6716	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6274	Approved
0.6692	Remote Similarity	NPD4730	Approved
0.6692	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6643	Remote Similarity	NPD8451	Approved
0.664	Remote Similarity	NPD6079	Approved
0.662	Remote Similarity	NPD7830	Approved
0.662	Remote Similarity	NPD7829	Approved
0.6619	Remote Similarity	NPD6313	Approved
0.6619	Remote Similarity	NPD6314	Approved
0.6617	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6845	Suspended
0.6597	Remote Similarity	NPD8448	Approved
0.6593	Remote Similarity	NPD5251	Approved
0.6593	Remote Similarity	NPD6371	Approved
0.6593	Remote Similarity	NPD5248	Approved
0.6593	Remote Similarity	NPD5247	Approved
0.6593	Remote Similarity	NPD5249	Phase 3
0.6593	Remote Similarity	NPD5250	Approved
0.6589	Remote Similarity	NPD4225	Approved
0.6581	Remote Similarity	NPD7625	Phase 1
0.6575	Remote Similarity	NPD8391	Approved
0.6575	Remote Similarity	NPD8392	Approved
0.6575	Remote Similarity	NPD8390	Approved
0.6565	Remote Similarity	NPD7632	Discontinued
0.656	Remote Similarity	NPD7838	Discovery
0.656	Remote Similarity	NPD6698	Approved
0.656	Remote Similarity	NPD46	Approved
0.6541	Remote Similarity	NPD4767	Approved
0.6541	Remote Similarity	NPD4768	Approved
0.6535	Remote Similarity	NPD7748	Approved
0.6512	Remote Similarity	NPD7902	Approved
0.6508	Remote Similarity	NPD5284	Approved
0.6508	Remote Similarity	NPD5281	Approved
0.6508	Remote Similarity	NPD6411	Approved
0.6508	Remote Similarity	NPD7983	Approved
0.65	Remote Similarity	NPD7641	Discontinued
0.6497	Remote Similarity	NPD7236	Approved
0.6493	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5695	Phase 3
0.648	Remote Similarity	NPD5328	Approved
0.6479	Remote Similarity	NPD6909	Approved
0.6479	Remote Similarity	NPD6908	Approved
0.6479	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5956	Approved
0.6462	Remote Similarity	NPD5696	Approved
0.6458	Remote Similarity	NPD8299	Approved
0.6458	Remote Similarity	NPD8341	Approved
0.6458	Remote Similarity	NPD8340	Approved
0.6458	Remote Similarity	NPD8342	Approved
0.6457	Remote Similarity	NPD6399	Phase 3
0.6457	Remote Similarity	NPD5779	Approved
0.6457	Remote Similarity	NPD5778	Approved
0.6457	Remote Similarity	NPD4202	Approved
0.6444	Remote Similarity	NPD5128	Approved
0.6434	Remote Similarity	NPD5222	Approved
0.6434	Remote Similarity	NPD5221	Approved
0.6434	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4697	Phase 3
0.6424	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5215	Approved
0.6423	Remote Similarity	NPD5217	Approved
0.6423	Remote Similarity	NPD5216	Approved
0.6416	Remote Similarity	NPD7685	Pre-registration
0.64	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7239	Suspended
0.6391	Remote Similarity	NPD4754	Approved
0.6389	Remote Similarity	NPD7642	Approved
0.6385	Remote Similarity	NPD5173	Approved
0.6378	Remote Similarity	NPD5693	Phase 1
0.6378	Remote Similarity	NPD7515	Phase 2
0.6378	Remote Similarity	NPD7637	Suspended
0.6371	Remote Similarity	NPD6684	Approved
0.6371	Remote Similarity	NPD7334	Approved
0.6371	Remote Similarity	NPD6409	Approved
0.6371	Remote Similarity	NPD7146	Approved
0.6371	Remote Similarity	NPD5330	Approved
0.6371	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD5344	Discontinued
0.6357	Remote Similarity	NPD6868	Approved
0.6357	Remote Similarity	NPD5210	Approved
0.6357	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD4629	Approved
0.635	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5135	Approved
0.635	Remote Similarity	NPD5169	Approved
0.6349	Remote Similarity	NPD4753	Phase 2
0.6349	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6101	Approved
0.6327	Remote Similarity	NPD8337	Approved
0.6327	Remote Similarity	NPD8336	Approved
0.632	Remote Similarity	NPD3573	Approved
0.6304	Remote Similarity	NPD5127	Approved
0.6303	Remote Similarity	NPD5760	Phase 2
0.6303	Remote Similarity	NPD5761	Phase 2

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