NPASS Compound

Structure

CID92885 OpenBabel06191715432D 34 39 0 0 1 0 0 0 0 0999 V2000 -1.2188 -4.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2260 -4.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2705 -2.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0504 -0.7523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6310 -1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0074 -1.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -2.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 -2.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8647 -1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0256 -2.6044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0501 -2.0275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -2.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7601 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1450 -1.6115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6310 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7521 -1.8673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8258 -3.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -1.9386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0074 -3.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1365 -1.9386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0646 -1.2185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0074 -4.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3756 -2.6491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 16 28 1 0 0 0 0 17 26 1 0 0 0 0 17 31 1 0 0 0 0 18 29 1 0 0 0 0 18 34 1 0 0 0 0 19 25 1 6 0 0 0 19 26 1 0 0 0 0 20 25 1 6 0 0 0 20 27 1 0 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 22 26 1 6 0 0 0 22 32 1 0 0 0 0 23 29 1 1 0 0 0 23 33 1 0 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 27 28 1 1 0 0 0 28 30 1 6 0 0 0 29 14 1 1 0 0 0 30 12 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	508.622
LogP:	4.269
LogD:	3.666
LogS:	-5.394
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	6.424
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.265
MDCK Permeability:	1.4377957995748147e-05
Pgp-inhibitor:	0.176
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	86.94603729248047%
Volume Distribution (VD):	0.985
Pgp-substrate:	5.2022480964660645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	5.278
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.654
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.199
Carcinogencity:	0.063
Eye Corrosion:	0.006
Eye Irritation:	0.03
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC92885

Natural Product ID:	NPC92885
*Common Name:**	IUBQSOTVBGNWDI-FYZNACKDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IUBQSOTVBGNWDI-FYZNACKDSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-24(2)13-14-29-18-34-30(21(29)15-24)12-8-20-25(3)10-9-22(32)26(4,17-31)19(25)7-11-27(20,5)28(30,6)16-23(29)33/h8,12,19-23,31-33H,7,9-11,13-18H2,1-6H3/t19-,20-,21-,22+,23-,25+,26+,27-,28+,29-,30+/m1/s1
SMILES:	CC1(C)CC[C@@]23CO[C@@]4(C=C[C@@H]5[C@@]6(C)CC[C@@H]([C@@](C)(CO)[C@@H]6CC[C@@]5(C)[C@]4(C)C[C@H]3O)O)[C@@H]2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3792450
PubChem CID:	21594258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9247.1	Bupleurum smithii var. parvifolium	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9247.1	Bupleurum smithii var. parvifolium	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	3

Activity Type	# Activity
Cell Line	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	80000.0	nM	PMID[482636]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	63350.0	nM	PMID[482636]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	>	80000.0	nM	PMID[482636]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	80000.0	nM	PMID[482636]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	70.04	%	PMID[482636]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	62.44	%	PMID[482636]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	62.58	%	PMID[482636]
NPT27	Others	Unspecified		IC50	>	80000.0	nM	PMID[482636]

☑ 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 NPC92885 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	198
0.1-0.2	1551
0.2-0.3	5190
0.3-0.4	14470
0.4-0.5	9263
0.5-0.6	5469
0.6-0.7	4848
0.7-0.8	1593
0.8-0.85	106
0.85-0.9	6
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC77796
1.0	High Similarity	NPC476226
0.8953	High Similarity	NPC477578
0.8824	High Similarity	NPC304285
0.8632	High Similarity	NPC235142
0.8605	High Similarity	NPC155521
0.8506	High Similarity	NPC470558
0.8485	Intermediate Similarity	NPC80210
0.8485	Intermediate Similarity	NPC38376
0.8421	Intermediate Similarity	NPC234617
0.8421	Intermediate Similarity	NPC124703
0.8409	Intermediate Similarity	NPC470077
0.84	Intermediate Similarity	NPC285253
0.84	Intermediate Similarity	NPC221110
0.84	Intermediate Similarity	NPC195116
0.84	Intermediate Similarity	NPC180459
0.8372	Intermediate Similarity	NPC295131
0.8353	Intermediate Similarity	NPC253807
0.8353	Intermediate Similarity	NPC230295
0.8353	Intermediate Similarity	NPC158662
0.8353	Intermediate Similarity	NPC300499
0.8353	Intermediate Similarity	NPC98386
0.8353	Intermediate Similarity	NPC196753
0.8333	Intermediate Similarity	NPC149224
0.8298	Intermediate Similarity	NPC477969
0.8298	Intermediate Similarity	NPC135224
0.8295	Intermediate Similarity	NPC253402
0.8295	Intermediate Similarity	NPC159168
0.828	Intermediate Similarity	NPC27531
0.8256	Intermediate Similarity	NPC291379
0.8256	Intermediate Similarity	NPC53744
0.8235	Intermediate Similarity	NPC110494
0.8235	Intermediate Similarity	NPC157474
0.8235	Intermediate Similarity	NPC169994
0.8235	Intermediate Similarity	NPC101475
0.8235	Intermediate Similarity	NPC40394
0.8235	Intermediate Similarity	NPC34177
0.8235	Intermediate Similarity	NPC157996
0.8202	Intermediate Similarity	NPC238992
0.8191	Intermediate Similarity	NPC189513
0.8191	Intermediate Similarity	NPC144202
0.8182	Intermediate Similarity	NPC47763
0.8182	Intermediate Similarity	NPC470049
0.8155	Intermediate Similarity	NPC476305
0.8155	Intermediate Similarity	NPC473125
0.8152	Intermediate Similarity	NPC187785
0.8152	Intermediate Similarity	NPC259875
0.8144	Intermediate Similarity	NPC474190
0.814	Intermediate Similarity	NPC470396
0.814	Intermediate Similarity	NPC99168
0.814	Intermediate Similarity	NPC22955
0.814	Intermediate Similarity	NPC11908
0.814	Intermediate Similarity	NPC474989
0.8132	Intermediate Similarity	NPC166857
0.8132	Intermediate Similarity	NPC470620
0.8118	Intermediate Similarity	NPC290598
0.8118	Intermediate Similarity	NPC27765
0.8118	Intermediate Similarity	NPC30590
0.8118	Intermediate Similarity	NPC265328
0.8118	Intermediate Similarity	NPC122418
0.8118	Intermediate Similarity	NPC120098
0.8111	Intermediate Similarity	NPC274448
0.8111	Intermediate Similarity	NPC266511
0.8111	Intermediate Similarity	NPC157257
0.8105	Intermediate Similarity	NPC8774
0.8105	Intermediate Similarity	NPC477970
0.8105	Intermediate Similarity	NPC100892
0.809	Intermediate Similarity	NPC237795
0.809	Intermediate Similarity	NPC82538
0.8077	Intermediate Similarity	NPC40133
0.8077	Intermediate Similarity	NPC290608
0.8077	Intermediate Similarity	NPC44298
0.8077	Intermediate Similarity	NPC473128
0.8077	Intermediate Similarity	NPC49413
0.8068	Intermediate Similarity	NPC116202
0.8068	Intermediate Similarity	NPC242350
0.8065	Intermediate Similarity	NPC295668
0.8061	Intermediate Similarity	NPC473160
0.8023	Intermediate Similarity	NPC470711
0.8023	Intermediate Similarity	NPC470750
0.8023	Intermediate Similarity	NPC470758
0.8022	Intermediate Similarity	NPC84121
0.8022	Intermediate Similarity	NPC137306
0.8022	Intermediate Similarity	NPC237344
0.8022	Intermediate Similarity	NPC299068
0.8021	Intermediate Similarity	NPC98457
0.8021	Intermediate Similarity	NPC12103
0.8021	Intermediate Similarity	NPC227583
0.8021	Intermediate Similarity	NPC288970
0.802	Intermediate Similarity	NPC301666
0.8	Intermediate Similarity	NPC65402
0.8	Intermediate Similarity	NPC138374
0.8	Intermediate Similarity	NPC127718
0.8	Intermediate Similarity	NPC34700
0.8	Intermediate Similarity	NPC91010
0.8	Intermediate Similarity	NPC205845
0.798	Intermediate Similarity	NPC37207
0.798	Intermediate Similarity	NPC283343
0.798	Intermediate Similarity	NPC258547
0.798	Intermediate Similarity	NPC471482
0.798	Intermediate Similarity	NPC273668
0.798	Intermediate Similarity	NPC300399
0.7978	Intermediate Similarity	NPC296701
0.7978	Intermediate Similarity	NPC218616
0.7959	Intermediate Similarity	NPC228251
0.7959	Intermediate Similarity	NPC161527
0.7959	Intermediate Similarity	NPC219285
0.7959	Intermediate Similarity	NPC477972
0.7959	Intermediate Similarity	NPC477968
0.7959	Intermediate Similarity	NPC477971
0.7959	Intermediate Similarity	NPC20113
0.7955	Intermediate Similarity	NPC322313
0.7955	Intermediate Similarity	NPC102253
0.7955	Intermediate Similarity	NPC236237
0.7938	Intermediate Similarity	NPC210337
0.7938	Intermediate Similarity	NPC10057
0.7938	Intermediate Similarity	NPC51499
0.7935	Intermediate Similarity	NPC476948
0.7917	Intermediate Similarity	NPC290481
0.7912	Intermediate Similarity	NPC191965
0.7912	Intermediate Similarity	NPC470360
0.7912	Intermediate Similarity	NPC318390
0.7907	Intermediate Similarity	NPC470749
0.7907	Intermediate Similarity	NPC106364
0.79	Intermediate Similarity	NPC471887
0.79	Intermediate Similarity	NPC471888
0.79	Intermediate Similarity	NPC471886
0.79	Intermediate Similarity	NPC471885
0.79	Intermediate Similarity	NPC473123
0.79	Intermediate Similarity	NPC473124
0.7895	Intermediate Similarity	NPC307776
0.7889	Intermediate Similarity	NPC82623
0.7889	Intermediate Similarity	NPC134481
0.7882	Intermediate Similarity	NPC91858
0.7882	Intermediate Similarity	NPC100334
0.7872	Intermediate Similarity	NPC471432
0.7872	Intermediate Similarity	NPC471433
0.7865	Intermediate Similarity	NPC474759
0.7865	Intermediate Similarity	NPC474683
0.7865	Intermediate Similarity	NPC82986
0.7865	Intermediate Similarity	NPC7505
0.7865	Intermediate Similarity	NPC474731
0.7865	Intermediate Similarity	NPC249423
0.7865	Intermediate Similarity	NPC476646
0.7865	Intermediate Similarity	NPC474752
0.7857	Intermediate Similarity	NPC164349
0.7857	Intermediate Similarity	NPC275086
0.7857	Intermediate Similarity	NPC325229
0.7849	Intermediate Similarity	NPC471952
0.7849	Intermediate Similarity	NPC4574
0.7849	Intermediate Similarity	NPC212596
0.7849	Intermediate Similarity	NPC475605
0.7841	Intermediate Similarity	NPC80530
0.7841	Intermediate Similarity	NPC273410
0.7835	Intermediate Similarity	NPC88009
0.7826	Intermediate Similarity	NPC139724
0.7826	Intermediate Similarity	NPC261266
0.7826	Intermediate Similarity	NPC6605
0.7826	Intermediate Similarity	NPC6391
0.7826	Intermediate Similarity	NPC173917
0.7822	Intermediate Similarity	NPC203354
0.7822	Intermediate Similarity	NPC110656
0.7822	Intermediate Similarity	NPC473127
0.7816	Intermediate Similarity	NPC470751
0.7816	Intermediate Similarity	NPC472805
0.7816	Intermediate Similarity	NPC90979
0.7816	Intermediate Similarity	NPC91594
0.7812	Intermediate Similarity	NPC105490
0.7802	Intermediate Similarity	NPC474047
0.78	Intermediate Similarity	NPC471889
0.7791	Intermediate Similarity	NPC291503
0.7789	Intermediate Similarity	NPC41554
0.7789	Intermediate Similarity	NPC97404
0.7778	Intermediate Similarity	NPC230546
0.7778	Intermediate Similarity	NPC473510
0.7778	Intermediate Similarity	NPC101462
0.7778	Intermediate Similarity	NPC87489
0.7778	Intermediate Similarity	NPC473790
0.7778	Intermediate Similarity	NPC49964
0.7778	Intermediate Similarity	NPC30166
0.7766	Intermediate Similarity	NPC138974
0.7766	Intermediate Similarity	NPC101886
0.7765	Intermediate Similarity	NPC253805
0.7765	Intermediate Similarity	NPC182717
0.7755	Intermediate Similarity	NPC476893
0.7755	Intermediate Similarity	NPC316604
0.7753	Intermediate Similarity	NPC96362
0.7745	Intermediate Similarity	NPC88349
0.7742	Intermediate Similarity	NPC304083
0.7742	Intermediate Similarity	NPC189777
0.7732	Intermediate Similarity	NPC83693
0.7732	Intermediate Similarity	NPC276110
0.7727	Intermediate Similarity	NPC167037
0.7727	Intermediate Similarity	NPC285761
0.7727	Intermediate Similarity	NPC244385
0.7727	Intermediate Similarity	NPC6978
0.7727	Intermediate Similarity	NPC148977
0.7727	Intermediate Similarity	NPC138621
0.7727	Intermediate Similarity	NPC72507
0.7723	Intermediate Similarity	NPC471450

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 NPC92885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1631
0.2-0.3	4175
0.3-0.4	2246
0.4-0.5	503
0.5-0.6	209
0.6-0.7	181
0.7-0.8	22
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD7645	Phase 2
0.7955	Intermediate Similarity	NPD7525	Registered
0.7327	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.7255	Intermediate Similarity	NPD7640	Approved
0.7255	Intermediate Similarity	NPD7639	Approved
0.7245	Intermediate Similarity	NPD7515	Phase 2
0.7228	Intermediate Similarity	NPD7902	Approved
0.7191	Intermediate Similarity	NPD7339	Approved
0.7191	Intermediate Similarity	NPD6942	Approved
0.7111	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7328	Approved
0.6991	Remote Similarity	NPD7327	Approved
0.699	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD6695	Phase 3
0.6931	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7900	Approved
0.693	Remote Similarity	NPD7516	Approved
0.6903	Remote Similarity	NPD7115	Discovery
0.687	Remote Similarity	NPD8294	Approved
0.687	Remote Similarity	NPD8377	Approved
0.6869	Remote Similarity	NPD6051	Approved
0.6837	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8264	Approved
0.681	Remote Similarity	NPD8296	Approved
0.681	Remote Similarity	NPD8335	Approved
0.681	Remote Similarity	NPD7503	Approved
0.681	Remote Similarity	NPD8379	Approved
0.681	Remote Similarity	NPD8033	Approved
0.681	Remote Similarity	NPD8380	Approved
0.681	Remote Similarity	NPD8378	Approved
0.6792	Remote Similarity	NPD5211	Phase 2
0.6789	Remote Similarity	NPD6899	Approved
0.6789	Remote Similarity	NPD6881	Approved
0.6762	Remote Similarity	NPD5285	Approved
0.6762	Remote Similarity	NPD4696	Approved
0.6762	Remote Similarity	NPD5286	Approved
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6759	Remote Similarity	NPD7128	Approved
0.6735	Remote Similarity	NPD3618	Phase 1
0.6733	Remote Similarity	NPD6079	Approved
0.6733	Remote Similarity	NPD8035	Phase 2
0.6733	Remote Similarity	NPD8034	Phase 2
0.6731	Remote Similarity	NPD4755	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4784	Approved
0.6703	Remote Similarity	NPD6926	Approved
0.6703	Remote Similarity	NPD6924	Approved
0.6703	Remote Similarity	NPD4785	Approved
0.6701	Remote Similarity	NPD4786	Approved
0.67	Remote Similarity	NPD5328	Approved
0.6698	Remote Similarity	NPD4159	Approved
0.6697	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6636	Remote Similarity	NPD5225	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7332	Phase 2
0.6632	Remote Similarity	NPD6930	Phase 2
0.6632	Remote Similarity	NPD7509	Discontinued
0.6632	Remote Similarity	NPD6931	Approved
0.6632	Remote Similarity	NPD7514	Phase 3
0.6629	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD6617	Approved
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6607	Remote Similarity	NPD6650	Approved
0.6607	Remote Similarity	NPD6649	Approved
0.6604	Remote Similarity	NPD4700	Approved
0.6596	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD6372	Approved
0.6577	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6574	Remote Similarity	NPD5174	Approved
0.6574	Remote Similarity	NPD5175	Approved
0.6559	Remote Similarity	NPD6933	Approved
0.6549	Remote Similarity	NPD8297	Approved
0.6549	Remote Similarity	NPD6882	Approved
0.6545	Remote Similarity	NPD5701	Approved
0.6542	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD5344	Discontinued
0.6526	Remote Similarity	NPD6929	Approved
0.6518	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6932	Approved
0.6486	Remote Similarity	NPD6011	Approved
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7151	Approved
0.6484	Remote Similarity	NPD7152	Approved
0.6484	Remote Similarity	NPD7150	Approved
0.6476	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5222	Approved
0.6476	Remote Similarity	NPD5221	Approved
0.6458	Remote Similarity	NPD4748	Discontinued
0.6446	Remote Similarity	NPD7507	Approved
0.6421	Remote Similarity	NPD7145	Approved
0.6415	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD5173	Approved
0.6415	Remote Similarity	NPD6083	Phase 2
0.6408	Remote Similarity	NPD7087	Discontinued
0.6395	Remote Similarity	NPD368	Approved
0.6392	Remote Similarity	NPD6902	Approved
0.6374	Remote Similarity	NPD7144	Approved
0.6374	Remote Similarity	NPD7143	Approved
0.6373	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD4195	Approved
0.6348	Remote Similarity	NPD8133	Approved
0.6339	Remote Similarity	NPD4730	Approved
0.6339	Remote Similarity	NPD6686	Approved
0.6339	Remote Similarity	NPD4729	Approved
0.6321	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5776	Phase 2
0.6316	Remote Similarity	NPD6925	Approved
0.6306	Remote Similarity	NPD4768	Approved
0.6306	Remote Similarity	NPD4767	Approved
0.6303	Remote Similarity	NPD6054	Approved
0.63	Remote Similarity	NPD1694	Approved
0.63	Remote Similarity	NPD6893	Approved
0.6296	Remote Similarity	NPD6648	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6277	Remote Similarity	NPD4190	Phase 3
0.6277	Remote Similarity	NPD5275	Approved
0.6275	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4754	Approved
0.6264	Remote Similarity	NPD6922	Approved
0.6264	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4519	Discontinued
0.6238	Remote Similarity	NPD4623	Approved
0.6228	Remote Similarity	NPD5248	Approved
0.6228	Remote Similarity	NPD5249	Phase 3
0.6228	Remote Similarity	NPD5251	Approved
0.6228	Remote Similarity	NPD4634	Approved
0.6228	Remote Similarity	NPD5247	Approved
0.6228	Remote Similarity	NPD5250	Approved
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6224	Remote Similarity	NPD6898	Phase 1
0.6218	Remote Similarity	NPD7101	Approved
0.6218	Remote Similarity	NPD7100	Approved
0.621	Remote Similarity	NPD7736	Approved
0.6204	Remote Similarity	NPD5290	Discontinued
0.62	Remote Similarity	NPD3668	Phase 3
0.62	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6370	Approved
0.6195	Remote Similarity	NPD5128	Approved
0.6186	Remote Similarity	NPD6683	Phase 2
0.6176	Remote Similarity	NPD3573	Approved
0.6174	Remote Similarity	NPD5215	Approved
0.6174	Remote Similarity	NPD5217	Approved
0.6174	Remote Similarity	NPD5216	Approved
0.6167	Remote Similarity	NPD6059	Approved
0.6162	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8328	Phase 3
0.614	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6335	Approved
0.6122	Remote Similarity	NPD6928	Phase 2
0.6116	Remote Similarity	NPD8515	Approved
0.6116	Remote Similarity	NPD8517	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD8513	Phase 3
0.6116	Remote Similarity	NPD6016	Approved
0.6116	Remote Similarity	NPD8516	Approved
0.6102	Remote Similarity	NPD6274	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6087	Remote Similarity	NPD5169	Approved
0.6087	Remote Similarity	NPD5135	Approved
0.6087	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7146	Approved
0.6078	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6684	Approved
0.6078	Remote Similarity	NPD7521	Approved
0.6078	Remote Similarity	NPD5330	Approved
0.6078	Remote Similarity	NPD6409	Approved
0.6078	Remote Similarity	NPD7334	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