NPASS Compound

Structure

NPC470697 OpenBabel07101718192D 29 30 0 0 1 0 0 0 0 0999 V2000 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 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 0.0000 1.0000 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 -2.5981 1.5000 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 -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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 2.5981 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 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 2.5981 1.5000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 12 2 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 22 1 1 0 0 0 15 16 1 0 0 0 0 16 23 2 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 24 2 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.2
Volume:	417.668
LogP:	2.447
LogD:	1.139
LogS:	-3.558
# Rotatable Bonds:	8
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	4.655
Fsp3:	0.636
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:	-4.617
MDCK Permeability:	1.8328155420022085e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	47.19568634033203%
Volume Distribution (VD):	0.614
Pgp-substrate:	61.31950759887695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.371
CYP2C19-inhibitor:	0.829
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	8.693
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.633
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.121
Carcinogencity:	0.096
Eye Corrosion:	0.023
Eye Irritation:	0.198
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC470697

Natural Product ID:	NPC470697
*Common Name:**	3-Beta-Angeloyloxy-8-Oxoeremophil-6(7)-Ene-12,15-Dioic Acid Methylester
IUPAC Name:	methyl (4aR,8aR)-7-(1-methoxy-1-oxopropan-2-yl)-8a-methyl-2-[(Z)-2-methylbut-2-enoyl]oxy-6-oxo-1,2,3,4,4a,5-hexahydronaphthalene-1-carboxylate
Synonyms:
Standard InCHIKey:	DDHBCBRLTQJJBD-MFQWHITESA-N
Standard InCHI:	InChI=1S/C22H30O7/c1-7-12(2)19(24)29-17-9-8-14-10-16(23)15(13(3)20(25)27-5)11-22(14,4)18(17)21(26)28-6/h7,11,13-14,17-18H,8-10H2,1-6H3/b12-7-/t13?,14-,17?,18?,22+/m1/s1
SMILES:	CC=C(C)C(=O)OC1CCC2CC(=O)C(=CC2(C1C(=O)OC)C)C(C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218575
PubChem CID:	44419530
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO283	Ligularia lapathifolia	Species	Asteraceae	Eukaryota	roots	n.a.	n.a.	PMID[17284071]
NPO283	Ligularia lapathifolia	Species	Asteraceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[501158]
NPT1317	Cell Line	CCRF S-180	Mus musculus	IC50	>	100000.0	nM	PMID[501158]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[501158]

☑ 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 NPC470697 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	227
0.1-0.2	1324
0.2-0.3	4280
0.3-0.4	8339
0.4-0.5	13763
0.5-0.6	7268
0.6-0.7	5544
0.7-0.8	1843
0.8-0.85	95
0.85-0.9	13
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC73995
0.8842	High Similarity	NPC476299
0.8842	High Similarity	NPC474012
0.8817	High Similarity	NPC183012
0.8791	High Similarity	NPC152467
0.8778	High Similarity	NPC215831
0.871	High Similarity	NPC38830
0.871	High Similarity	NPC477129
0.871	High Similarity	NPC477130
0.8696	High Similarity	NPC473944
0.8673	High Similarity	NPC470297
0.8652	High Similarity	NPC189311
0.8632	High Similarity	NPC2049
0.8587	High Similarity	NPC161638
0.8587	High Similarity	NPC8062
0.8586	High Similarity	NPC1679
0.8571	High Similarity	NPC477128
0.8571	High Similarity	NPC226863
0.8556	High Similarity	NPC220478
0.8542	High Similarity	NPC316598
0.8539	High Similarity	NPC30486
0.8526	High Similarity	NPC242848
0.8511	High Similarity	NPC84893
0.8485	Intermediate Similarity	NPC189616
0.8469	Intermediate Similarity	NPC40918
0.8454	Intermediate Similarity	NPC475202
0.8454	Intermediate Similarity	NPC475392
0.8454	Intermediate Similarity	NPC475385
0.8444	Intermediate Similarity	NPC177932
0.8438	Intermediate Similarity	NPC110937
0.8438	Intermediate Similarity	NPC38530
0.8438	Intermediate Similarity	NPC84335
0.8427	Intermediate Similarity	NPC193198
0.8427	Intermediate Similarity	NPC22611
0.8421	Intermediate Similarity	NPC476519
0.8416	Intermediate Similarity	NPC89171
0.8416	Intermediate Similarity	NPC476802
0.8404	Intermediate Similarity	NPC475657
0.8404	Intermediate Similarity	NPC139692
0.8404	Intermediate Similarity	NPC115021
0.8387	Intermediate Similarity	NPC220454
0.8387	Intermediate Similarity	NPC469595
0.8387	Intermediate Similarity	NPC212679
0.8384	Intermediate Similarity	NPC476889
0.8367	Intermediate Similarity	NPC476888
0.8367	Intermediate Similarity	NPC93744
0.8351	Intermediate Similarity	NPC264378
0.8351	Intermediate Similarity	NPC252295
0.8351	Intermediate Similarity	NPC478056
0.8333	Intermediate Similarity	NPC159635
0.8333	Intermediate Similarity	NPC202833
0.8316	Intermediate Similarity	NPC476596
0.8315	Intermediate Similarity	NPC186276
0.8315	Intermediate Similarity	NPC178676
0.8298	Intermediate Similarity	NPC72845
0.8298	Intermediate Similarity	NPC186363
0.8298	Intermediate Similarity	NPC49420
0.8298	Intermediate Similarity	NPC233345
0.8283	Intermediate Similarity	NPC476890
0.828	Intermediate Similarity	NPC168131
0.828	Intermediate Similarity	NPC5509
0.828	Intermediate Similarity	NPC288699
0.828	Intermediate Similarity	NPC284561
0.8265	Intermediate Similarity	NPC117685
0.8265	Intermediate Similarity	NPC473219
0.8265	Intermediate Similarity	NPC470761
0.8265	Intermediate Similarity	NPC476933
0.8247	Intermediate Similarity	NPC73911
0.8247	Intermediate Similarity	NPC474343
0.8247	Intermediate Similarity	NPC226986
0.8242	Intermediate Similarity	NPC476678
0.8242	Intermediate Similarity	NPC110405
0.8229	Intermediate Similarity	NPC274417
0.8222	Intermediate Similarity	NPC222358
0.8211	Intermediate Similarity	NPC271652
0.8211	Intermediate Similarity	NPC476598
0.8211	Intermediate Similarity	NPC476597
0.8202	Intermediate Similarity	NPC282293
0.8202	Intermediate Similarity	NPC475665
0.82	Intermediate Similarity	NPC132395
0.82	Intermediate Similarity	NPC329345
0.82	Intermediate Similarity	NPC471364
0.82	Intermediate Similarity	NPC475526
0.82	Intermediate Similarity	NPC254202
0.82	Intermediate Similarity	NPC95899
0.82	Intermediate Similarity	NPC471365
0.82	Intermediate Similarity	NPC473283
0.8191	Intermediate Similarity	NPC101651
0.8191	Intermediate Similarity	NPC159748
0.8191	Intermediate Similarity	NPC51486
0.819	Intermediate Similarity	NPC122056
0.8182	Intermediate Similarity	NPC473514
0.8173	Intermediate Similarity	NPC474315
0.8173	Intermediate Similarity	NPC470960
0.8172	Intermediate Similarity	NPC473229
0.8163	Intermediate Similarity	NPC278386
0.8163	Intermediate Similarity	NPC124512
0.8163	Intermediate Similarity	NPC216478
0.8163	Intermediate Similarity	NPC159763
0.8163	Intermediate Similarity	NPC176845
0.8144	Intermediate Similarity	NPC106425
0.8144	Intermediate Similarity	NPC122324
0.8144	Intermediate Similarity	NPC151725
0.8144	Intermediate Similarity	NPC307164
0.8144	Intermediate Similarity	NPC234993
0.8144	Intermediate Similarity	NPC134072
0.8137	Intermediate Similarity	NPC91034
0.8137	Intermediate Similarity	NPC133422
0.8132	Intermediate Similarity	NPC219011
0.8132	Intermediate Similarity	NPC470011
0.8125	Intermediate Similarity	NPC473435
0.8125	Intermediate Similarity	NPC53685
0.8125	Intermediate Similarity	NPC269729
0.8125	Intermediate Similarity	NPC473431
0.8125	Intermediate Similarity	NPC471078
0.8125	Intermediate Similarity	NPC476415
0.8125	Intermediate Similarity	NPC473280
0.8119	Intermediate Similarity	NPC146731
0.8119	Intermediate Similarity	NPC118911
0.8113	Intermediate Similarity	NPC147912
0.8113	Intermediate Similarity	NPC67259
0.8111	Intermediate Similarity	NPC471218
0.8111	Intermediate Similarity	NPC200513
0.8111	Intermediate Similarity	NPC226988
0.8105	Intermediate Similarity	NPC472814
0.8105	Intermediate Similarity	NPC177037
0.8105	Intermediate Similarity	NPC252433
0.8105	Intermediate Similarity	NPC65513
0.81	Intermediate Similarity	NPC32577
0.81	Intermediate Similarity	NPC155332
0.81	Intermediate Similarity	NPC320447
0.81	Intermediate Similarity	NPC80781
0.81	Intermediate Similarity	NPC476081
0.81	Intermediate Similarity	NPC114540
0.8095	Intermediate Similarity	NPC69291
0.8095	Intermediate Similarity	NPC476801
0.809	Intermediate Similarity	NPC195424
0.8085	Intermediate Similarity	NPC280833
0.8081	Intermediate Similarity	NPC174314
0.8081	Intermediate Similarity	NPC47024
0.8081	Intermediate Similarity	NPC470906
0.8077	Intermediate Similarity	NPC253906
0.8065	Intermediate Similarity	NPC181327
0.8065	Intermediate Similarity	NPC175293
0.8061	Intermediate Similarity	NPC89225
0.8061	Intermediate Similarity	NPC287668
0.8061	Intermediate Similarity	NPC253826
0.8061	Intermediate Similarity	NPC53844
0.8061	Intermediate Similarity	NPC26413
0.8061	Intermediate Similarity	NPC170131
0.8058	Intermediate Similarity	NPC322903
0.8058	Intermediate Similarity	NPC473482
0.8058	Intermediate Similarity	NPC475418
0.8058	Intermediate Similarity	NPC318363
0.8058	Intermediate Similarity	NPC473483
0.8041	Intermediate Similarity	NPC209355
0.8039	Intermediate Similarity	NPC477125
0.8037	Intermediate Similarity	NPC64318
0.8022	Intermediate Similarity	NPC194637
0.8021	Intermediate Similarity	NPC79117
0.8021	Intermediate Similarity	NPC474185
0.802	Intermediate Similarity	NPC120321
0.802	Intermediate Similarity	NPC72151
0.802	Intermediate Similarity	NPC478057
0.802	Intermediate Similarity	NPC159533
0.8019	Intermediate Similarity	NPC159333
0.8	Intermediate Similarity	NPC474842
0.8	Intermediate Similarity	NPC469372
0.8	Intermediate Similarity	NPC38642
0.8	Intermediate Similarity	NPC471325
0.8	Intermediate Similarity	NPC25554
0.8	Intermediate Similarity	NPC81530
0.8	Intermediate Similarity	NPC115862
0.8	Intermediate Similarity	NPC194028
0.8	Intermediate Similarity	NPC472637
0.8	Intermediate Similarity	NPC168319
0.8	Intermediate Similarity	NPC475776
0.8	Intermediate Similarity	NPC475965
0.7981	Intermediate Similarity	NPC475065
0.798	Intermediate Similarity	NPC23364
0.798	Intermediate Similarity	NPC57079
0.798	Intermediate Similarity	NPC108368
0.7979	Intermediate Similarity	NPC80335
0.7979	Intermediate Similarity	NPC48107
0.7979	Intermediate Similarity	NPC277771
0.7979	Intermediate Similarity	NPC104560
0.7979	Intermediate Similarity	NPC477302
0.7978	Intermediate Similarity	NPC150646
0.7978	Intermediate Similarity	NPC178277
0.7963	Intermediate Similarity	NPC312824
0.7963	Intermediate Similarity	NPC167606
0.7963	Intermediate Similarity	NPC243065
0.7963	Intermediate Similarity	NPC470492
0.7963	Intermediate Similarity	NPC140055
0.7963	Intermediate Similarity	NPC286528
0.7963	Intermediate Similarity	NPC20302
0.7963	Intermediate Similarity	NPC470493
0.7963	Intermediate Similarity	NPC183580
0.7961	Intermediate Similarity	NPC143609
0.7961	Intermediate Similarity	NPC475570

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 NPC470697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1648
0.2-0.3	3606
0.3-0.4	2309
0.4-0.5	910
0.5-0.6	275
0.6-0.7	173
0.7-0.8	23
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
0.8444	Intermediate Similarity	NPD1694	Approved
0.8163	Intermediate Similarity	NPD4225	Approved
0.8125	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7900	Approved
0.8111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7115	Discovery
0.7879	Intermediate Similarity	NPD7902	Approved
0.7755	Intermediate Similarity	NPD7748	Approved
0.7684	Intermediate Similarity	NPD3573	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.7579	Intermediate Similarity	NPD6684	Approved
0.7579	Intermediate Similarity	NPD7334	Approved
0.7579	Intermediate Similarity	NPD5330	Approved
0.7579	Intermediate Similarity	NPD7521	Approved
0.7579	Intermediate Similarity	NPD6409	Approved
0.7579	Intermediate Similarity	NPD7146	Approved
0.7551	Intermediate Similarity	NPD7515	Phase 2
0.7453	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7638	Approved
0.7423	Intermediate Similarity	NPD5737	Approved
0.7423	Intermediate Similarity	NPD6903	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6672	Approved
0.7396	Intermediate Similarity	NPD3618	Phase 1
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7374	Intermediate Similarity	NPD5693	Phase 1
0.7358	Intermediate Similarity	NPD6008	Approved
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7327	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6373	Approved
0.7315	Intermediate Similarity	NPD6372	Approved
0.729	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD5785	Approved
0.7248	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.7216	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6411	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7158	Intermediate Similarity	NPD5209	Approved
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7156	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.7115	Intermediate Similarity	NPD5696	Approved
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7087	Intermediate Similarity	NPD4697	Phase 3
0.7064	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6011	Approved
0.7059	Intermediate Similarity	NPD6001	Approved
0.703	Intermediate Similarity	NPD6079	Approved
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD6869	Approved
0.7027	Intermediate Similarity	NPD8130	Phase 1
0.7019	Intermediate Similarity	NPD6083	Phase 2
0.7019	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD6080	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6101	Approved
0.6979	Remote Similarity	NPD3667	Approved
0.6964	Remote Similarity	NPD8297	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6957	Remote Similarity	NPD8039	Approved
0.6947	Remote Similarity	NPD4695	Discontinued
0.6931	Remote Similarity	NPD5692	Phase 3
0.6931	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5222	Approved
0.6916	Remote Similarity	NPD5211	Phase 2
0.6909	Remote Similarity	NPD6686	Approved
0.69	Remote Similarity	NPD5208	Approved
0.6887	Remote Similarity	NPD4696	Approved
0.6887	Remote Similarity	NPD5286	Approved
0.6887	Remote Similarity	NPD5285	Approved
0.6863	Remote Similarity	NPD5694	Approved
0.6863	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD8034	Phase 2
0.6863	Remote Similarity	NPD6050	Approved
0.6857	Remote Similarity	NPD5173	Approved
0.6857	Remote Similarity	NPD4755	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD3666	Approved
0.6837	Remote Similarity	NPD4786	Approved
0.6837	Remote Similarity	NPD3133	Approved
0.6837	Remote Similarity	NPD3665	Phase 1
0.6832	Remote Similarity	NPD6051	Approved
0.6796	Remote Similarity	NPD4202	Approved
0.6789	Remote Similarity	NPD5141	Approved
0.6786	Remote Similarity	NPD6371	Approved
0.6783	Remote Similarity	NPD6274	Approved
0.6768	Remote Similarity	NPD5363	Approved
0.6759	Remote Similarity	NPD5224	Approved
0.6759	Remote Similarity	NPD5225	Approved
0.6759	Remote Similarity	NPD7632	Discontinued
0.6759	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD4633	Approved
0.6757	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4700	Approved
0.6726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6098	Approved
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD5284	Approved
0.6697	Remote Similarity	NPD5174	Approved
0.6697	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6638	Remote Similarity	NPD6868	Approved
0.6637	Remote Similarity	NPD4634	Approved
0.6612	Remote Similarity	NPD7492	Approved
0.661	Remote Similarity	NPD7100	Approved
0.661	Remote Similarity	NPD7101	Approved
0.6609	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD7732	Phase 3
0.6602	Remote Similarity	NPD46	Approved
0.6602	Remote Similarity	NPD6698	Approved
0.6581	Remote Similarity	NPD6317	Approved
0.6574	Remote Similarity	NPD6648	Approved
0.6571	Remote Similarity	NPD5282	Discontinued
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6549	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7637	Suspended
0.6535	Remote Similarity	NPD4519	Discontinued
0.6535	Remote Similarity	NPD4623	Approved
0.6535	Remote Similarity	NPD5786	Approved
0.6535	Remote Similarity	NPD5279	Phase 3
0.6532	Remote Similarity	NPD7319	Approved
0.6525	Remote Similarity	NPD6314	Approved
0.6525	Remote Similarity	NPD6313	Approved
0.6525	Remote Similarity	NPD6335	Approved
0.6522	Remote Similarity	NPD4691	Approved
0.6522	Remote Similarity	NPD6053	Discontinued
0.6518	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5344	Discontinued
0.6509	Remote Similarity	NPD5654	Approved
0.6505	Remote Similarity	NPD1695	Approved
0.6504	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6015	Approved
0.65	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4221	Approved
0.6465	Remote Similarity	NPD4223	Phase 3
0.6465	Remote Similarity	NPD4270	Approved
0.6465	Remote Similarity	NPD4269	Approved
0.646	Remote Similarity	NPD5128	Approved
0.646	Remote Similarity	NPD4730	Approved
0.646	Remote Similarity	NPD4729	Approved
0.6452	Remote Similarity	NPD7736	Approved
0.6446	Remote Similarity	NPD6370	Approved
0.6446	Remote Similarity	NPD5988	Approved
0.6441	Remote Similarity	NPD6009	Approved
0.6436	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4768	Approved
0.6429	Remote Similarity	NPD4767	Approved
0.6423	Remote Similarity	NPD7507	Approved
0.6417	Remote Similarity	NPD6059	Approved
0.6413	Remote Similarity	NPD4137	Phase 3
0.6396	Remote Similarity	NPD4754	Approved
0.6396	Remote Similarity	NPD6052	Approved
0.6389	Remote Similarity	NPD5959	Approved
0.6373	Remote Similarity	NPD5690	Phase 2
0.6372	Remote Similarity	NPD6614	Approved
0.6372	Remote Similarity	NPD6412	Phase 2
0.6371	Remote Similarity	NPD8293	Discontinued
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6908	Approved
0.6364	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6348	Remote Similarity	NPD5249	Phase 3
0.6348	Remote Similarity	NPD5248	Approved
0.6348	Remote Similarity	NPD5247	Approved
0.6348	Remote Similarity	NPD5250	Approved
0.6348	Remote Similarity	NPD5251	Approved
0.6344	Remote Similarity	NPD4747	Approved
0.6337	Remote Similarity	NPD4197	Approved
0.6333	Remote Similarity	NPD2685	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data