NPASS Compound

Structure

NPC470346 OpenBabel07101718322D 27 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1299 0.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9286 1.5007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 0.4945 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 2.7577 -1.1146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1691 0.5300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7796 -0.9067 0.0000 C 0 0 1 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 -2.0000 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 -2.5981 -0.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.1636 0.0000 C 0 0 1 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 15 13 1 1 0 0 0 15 17 1 0 0 0 0 16 23 1 1 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 26 2 0 0 0 0 23 14 1 1 0 0 0 24 10 1 6 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.27
Volume:	407.896
LogP:	4.532
LogD:	4.072
LogS:	-5.113
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	5.317
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989
MDCK Permeability:	1.4436644960369449e-05
Pgp-inhibitor:	0.366
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.159
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.254
Plasma Protein Binding (PPB):	92.81852722167969%
Volume Distribution (VD):	1.561
Pgp-substrate:	5.366377830505371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.668
CYP2C19-inhibitor:	0.766
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.622
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.231
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	5.971
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.765
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.645
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.819
Carcinogencity:	0.632
Eye Corrosion:	0.045
Eye Irritation:	0.17
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC470346

Natural Product ID:	NPC470346
*Common Name:**	Rel-Myrtucommulone L
IUPAC Name:	(1'R,2R,4S,5'S)-6,6,8,8-tetramethyl-1',4-di(propan-2-yl)spiro[3,4-dihydrochromene-2,4'-bicyclo[3.1.0]hexane]-5,7-dione
Synonyms:	Rel-Myrtucommulone L
Standard InCHIKey:	QLGACJMERDLYGD-QBGYIRFESA-N
Standard InCHI:	InChI=1S/C24H36O3/c1-13(2)15-11-24(10-9-23(14(3)4)12-16(23)24)27-19-17(15)18(25)21(5,6)20(26)22(19,7)8/h13-16H,9-12H2,1-8H3/t15-,16-,23+,24+/m0/s1
SMILES:	CC([C@@H]1C[C@@]2(CC[C@]3([C@@H]2C3)C(C)C)OC2=C1C(=O)C(C(=O)C2(C)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011678
PubChem CID:	57333287
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499325]
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22276775]
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	IC50	=	41400.0	nM	PMID[543437]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	560000.0	nM	PMID[543437]

☑ 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 NPC470346 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	268
0.1-0.2	2396
0.2-0.3	10046
0.3-0.4	14894
0.4-0.5	8649
0.5-0.6	5348
0.6-0.7	1051
0.7-0.8	40
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC478243
0.8966	High Similarity	NPC478244
0.8851	High Similarity	NPC478258
0.8851	High Similarity	NPC478257
0.8391	Intermediate Similarity	NPC470345
0.7882	Intermediate Similarity	NPC478247
0.7882	Intermediate Similarity	NPC478246
0.7667	Intermediate Similarity	NPC478245
0.7526	Intermediate Similarity	NPC477268
0.7526	Intermediate Similarity	NPC472689
0.7526	Intermediate Similarity	NPC472690
0.7526	Intermediate Similarity	NPC477267
0.75	Intermediate Similarity	NPC38885
0.75	Intermediate Similarity	NPC279667
0.7471	Intermediate Similarity	NPC469996
0.7447	Intermediate Similarity	NPC280592
0.7447	Intermediate Similarity	NPC253177
0.7447	Intermediate Similarity	NPC213636
0.7444	Intermediate Similarity	NPC472492
0.7419	Intermediate Similarity	NPC143025
0.7416	Intermediate Similarity	NPC478262
0.7368	Intermediate Similarity	NPC471329
0.7368	Intermediate Similarity	NPC296114
0.7363	Intermediate Similarity	NPC472480
0.734	Intermediate Similarity	NPC305039
0.734	Intermediate Similarity	NPC473039
0.7333	Intermediate Similarity	NPC477271
0.7333	Intermediate Similarity	NPC477270
0.7333	Intermediate Similarity	NPC193347
0.7333	Intermediate Similarity	NPC477269
0.7333	Intermediate Similarity	NPC129080
0.7273	Intermediate Similarity	NPC23778
0.7245	Intermediate Similarity	NPC472733
0.7245	Intermediate Similarity	NPC472734
0.7234	Intermediate Similarity	NPC472677
0.7234	Intermediate Similarity	NPC58532
0.7222	Intermediate Similarity	NPC472684
0.7222	Intermediate Similarity	NPC44963
0.7204	Intermediate Similarity	NPC472491
0.7204	Intermediate Similarity	NPC472494
0.7204	Intermediate Similarity	NPC195640
0.7176	Intermediate Similarity	NPC144627
0.7174	Intermediate Similarity	NPC109512
0.7174	Intermediate Similarity	NPC475796
0.7174	Intermediate Similarity	NPC144258
0.7172	Intermediate Similarity	NPC27105
0.7172	Intermediate Similarity	NPC472732
0.7172	Intermediate Similarity	NPC472731
0.7157	Intermediate Similarity	NPC36321
0.7129	Intermediate Similarity	NPC475867
0.7129	Intermediate Similarity	NPC270155
0.7128	Intermediate Similarity	NPC472482
0.7128	Intermediate Similarity	NPC472484
0.7128	Intermediate Similarity	NPC472493
0.7128	Intermediate Similarity	NPC472481
0.7113	Intermediate Similarity	NPC472226
0.7113	Intermediate Similarity	NPC472225
0.71	Intermediate Similarity	NPC472687
0.71	Intermediate Similarity	NPC471331
0.71	Intermediate Similarity	NPC472730
0.71	Intermediate Similarity	NPC471330
0.71	Intermediate Similarity	NPC147954
0.71	Intermediate Similarity	NPC203388
0.71	Intermediate Similarity	NPC99657
0.71	Intermediate Similarity	NPC472729
0.71	Intermediate Similarity	NPC177680
0.71	Intermediate Similarity	NPC153776
0.7097	Intermediate Similarity	NPC323765
0.7097	Intermediate Similarity	NPC202868
0.7087	Intermediate Similarity	NPC13385
0.7065	Intermediate Similarity	NPC477373
0.7065	Intermediate Similarity	NPC271784
0.7059	Intermediate Similarity	NPC308351
0.7059	Intermediate Similarity	NPC271266
0.7053	Intermediate Similarity	NPC472483
0.7053	Intermediate Similarity	NPC131470
0.7053	Intermediate Similarity	NPC328313
0.7053	Intermediate Similarity	NPC80335
0.7053	Intermediate Similarity	NPC478261
0.7053	Intermediate Similarity	NPC53911
0.7053	Intermediate Similarity	NPC478259
0.7053	Intermediate Similarity	NPC143767
0.7053	Intermediate Similarity	NPC478260
0.7045	Intermediate Similarity	NPC124289
0.7045	Intermediate Similarity	NPC141346
0.7045	Intermediate Similarity	NPC142759
0.7045	Intermediate Similarity	NPC25908
0.7045	Intermediate Similarity	NPC226242
0.7045	Intermediate Similarity	NPC115719
0.7045	Intermediate Similarity	NPC473437
0.7041	Intermediate Similarity	NPC294266
0.7041	Intermediate Similarity	NPC124207
0.7033	Intermediate Similarity	NPC189237
0.7033	Intermediate Similarity	NPC477372
0.7033	Intermediate Similarity	NPC150506
0.703	Intermediate Similarity	NPC472727
0.703	Intermediate Similarity	NPC472728
0.703	Intermediate Similarity	NPC112167
0.7021	Intermediate Similarity	NPC477478
0.7021	Intermediate Similarity	NPC472488
0.7021	Intermediate Similarity	NPC477479
0.7021	Intermediate Similarity	NPC472479
0.7011	Intermediate Similarity	NPC469691
0.7011	Intermediate Similarity	NPC167049
0.7011	Intermediate Similarity	NPC255021
0.701	Intermediate Similarity	NPC218301
0.7	Intermediate Similarity	NPC151488
0.7	Intermediate Similarity	NPC469608
0.7	Intermediate Similarity	NPC32758
0.7	Intermediate Similarity	NPC20078
0.7	Intermediate Similarity	NPC301769
0.7	Intermediate Similarity	NPC473574
0.699	Remote Similarity	NPC474330
0.699	Remote Similarity	NPC474207
0.6989	Remote Similarity	NPC469407
0.6979	Remote Similarity	NPC86319
0.6979	Remote Similarity	NPC477943
0.6979	Remote Similarity	NPC275740
0.6977	Remote Similarity	NPC5701
0.697	Remote Similarity	NPC31021
0.6961	Remote Similarity	NPC181645
0.6957	Remote Similarity	NPC321289
0.6957	Remote Similarity	NPC327969
0.6957	Remote Similarity	NPC100297
0.6957	Remote Similarity	NPC469325
0.6952	Remote Similarity	NPC220974
0.6944	Remote Similarity	NPC476163
0.6939	Remote Similarity	NPC474807
0.6939	Remote Similarity	NPC25750
0.6932	Remote Similarity	NPC77501
0.6932	Remote Similarity	NPC251435
0.6932	Remote Similarity	NPC475771
0.6932	Remote Similarity	NPC469669
0.6932	Remote Similarity	NPC469678
0.6923	Remote Similarity	NPC164218
0.6923	Remote Similarity	NPC287817
0.6923	Remote Similarity	NPC74445
0.6923	Remote Similarity	NPC235889
0.6923	Remote Similarity	NPC47747
0.6915	Remote Similarity	NPC469948
0.6915	Remote Similarity	NPC473038
0.6907	Remote Similarity	NPC183283
0.6907	Remote Similarity	NPC161638
0.6907	Remote Similarity	NPC223093
0.69	Remote Similarity	NPC272411
0.69	Remote Similarity	NPC125622
0.69	Remote Similarity	NPC95565
0.69	Remote Similarity	NPC21681
0.69	Remote Similarity	NPC472675
0.6897	Remote Similarity	NPC107783
0.6897	Remote Similarity	NPC92909
0.6893	Remote Similarity	NPC163249
0.6889	Remote Similarity	NPC222210
0.6889	Remote Similarity	NPC63445
0.6889	Remote Similarity	NPC476808
0.6882	Remote Similarity	NPC476082
0.6882	Remote Similarity	NPC8091
0.6882	Remote Similarity	NPC469561
0.6882	Remote Similarity	NPC278648
0.6875	Remote Similarity	NPC471724
0.6875	Remote Similarity	NPC241507
0.6875	Remote Similarity	NPC328539
0.6875	Remote Similarity	NPC28227
0.6875	Remote Similarity	NPC269677
0.6869	Remote Similarity	NPC469819
0.6869	Remote Similarity	NPC114162
0.6869	Remote Similarity	NPC184870
0.6869	Remote Similarity	NPC318332
0.6867	Remote Similarity	NPC61473
0.6863	Remote Similarity	NPC474720
0.6863	Remote Similarity	NPC83709
0.6857	Remote Similarity	NPC60681
0.6857	Remote Similarity	NPC470267
0.6857	Remote Similarity	NPC181265
0.6854	Remote Similarity	NPC69408
0.6854	Remote Similarity	NPC182848
0.6852	Remote Similarity	NPC43775
0.6848	Remote Similarity	NPC282293
0.6848	Remote Similarity	NPC474353
0.6842	Remote Similarity	NPC474733
0.6842	Remote Similarity	NPC145879
0.6842	Remote Similarity	NPC31564
0.6842	Remote Similarity	NPC72133
0.6842	Remote Similarity	NPC474778
0.6842	Remote Similarity	NPC474732
0.6837	Remote Similarity	NPC150383
0.6837	Remote Similarity	NPC190442
0.6837	Remote Similarity	NPC63748
0.6832	Remote Similarity	NPC18319
0.6832	Remote Similarity	NPC23680
0.6832	Remote Similarity	NPC18509
0.6832	Remote Similarity	NPC216904
0.6827	Remote Similarity	NPC470954
0.6822	Remote Similarity	NPC474901
0.6822	Remote Similarity	NPC475941
0.6822	Remote Similarity	NPC470257
0.6813	Remote Similarity	NPC215843
0.6813	Remote Similarity	NPC477371
0.6809	Remote Similarity	NPC329043
0.6809	Remote Similarity	NPC321187

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 NPC470346 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	3002
0.2-0.3	4057
0.3-0.4	1269
0.4-0.5	280
0.5-0.6	154
0.6-0.7	119
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.734	Intermediate Similarity	NPD6673	Approved
0.734	Intermediate Similarity	NPD6080	Approved
0.734	Intermediate Similarity	NPD6904	Approved
0.7333	Intermediate Similarity	NPD4221	Approved
0.7333	Intermediate Similarity	NPD4223	Phase 3
0.732	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5329	Approved
0.7234	Intermediate Similarity	NPD5208	Approved
0.7216	Intermediate Similarity	NPD6001	Approved
0.7204	Intermediate Similarity	NPD7146	Approved
0.7204	Intermediate Similarity	NPD7334	Approved
0.7204	Intermediate Similarity	NPD6684	Approved
0.7204	Intermediate Similarity	NPD6409	Approved
0.7204	Intermediate Similarity	NPD5330	Approved
0.7204	Intermediate Similarity	NPD6098	Approved
0.7204	Intermediate Similarity	NPD7521	Approved
0.7188	Intermediate Similarity	NPD6050	Approved
0.7174	Intermediate Similarity	NPD4197	Approved
0.7083	Intermediate Similarity	NPD5207	Approved
0.7083	Intermediate Similarity	NPD5692	Phase 3
0.7079	Intermediate Similarity	NPD3617	Approved
0.7053	Intermediate Similarity	NPD6903	Approved
0.7053	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4692	Approved
0.7033	Intermediate Similarity	NPD4139	Approved
0.7021	Intermediate Similarity	NPD5690	Phase 2
0.7021	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4694	Approved
0.7021	Intermediate Similarity	NPD4689	Approved
0.7021	Intermediate Similarity	NPD5205	Approved
0.7021	Intermediate Similarity	NPD4688	Approved
0.7021	Intermediate Similarity	NPD5280	Approved
0.7021	Intermediate Similarity	NPD4138	Approved
0.7021	Intermediate Similarity	NPD4693	Phase 3
0.7021	Intermediate Similarity	NPD4690	Approved
0.701	Intermediate Similarity	NPD5694	Approved
0.701	Intermediate Similarity	NPD5693	Phase 1
0.7	Intermediate Similarity	NPD5959	Approved
0.6979	Remote Similarity	NPD5328	Approved
0.6939	Remote Similarity	NPD5133	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6672	Approved
0.6867	Remote Similarity	NPD7341	Phase 2
0.6857	Remote Similarity	NPD7128	Approved
0.6857	Remote Similarity	NPD6675	Approved
0.6857	Remote Similarity	NPD6008	Approved
0.6857	Remote Similarity	NPD6402	Approved
0.6857	Remote Similarity	NPD5739	Approved
0.6837	Remote Similarity	NPD6079	Approved
0.6832	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD4755	Approved
0.6832	Remote Similarity	NPD6083	Phase 2
0.6809	Remote Similarity	NPD3665	Phase 1
0.6809	Remote Similarity	NPD3666	Approved
0.6809	Remote Similarity	NPD3133	Approved
0.6804	Remote Similarity	NPD4753	Phase 2
0.68	Remote Similarity	NPD5695	Phase 3
0.68	Remote Similarity	NPD5654	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6768	Remote Similarity	NPD4202	Approved
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD7320	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6702	Remote Similarity	NPD4788	Approved
0.6699	Remote Similarity	NPD5285	Approved
0.6699	Remote Similarity	NPD5286	Approved
0.6699	Remote Similarity	NPD4700	Approved
0.6699	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6635	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD4786	Approved
0.663	Remote Similarity	NPD4195	Approved
0.6629	Remote Similarity	NPD5733	Approved
0.6606	Remote Similarity	NPD7290	Approved
0.6606	Remote Similarity	NPD7102	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.6602	Remote Similarity	NPD5696	Approved
0.6596	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD4633	Approved
0.6571	Remote Similarity	NPD5225	Approved
0.6571	Remote Similarity	NPD5211	Phase 2
0.6571	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD5226	Approved
0.6566	Remote Similarity	NPD4096	Approved
0.6552	Remote Similarity	NPD4137	Phase 3
0.6545	Remote Similarity	NPD6617	Approved
0.6545	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6869	Approved
0.6545	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4518	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6509	Remote Similarity	NPD5174	Approved
0.6509	Remote Similarity	NPD6052	Approved
0.6509	Remote Similarity	NPD4754	Approved
0.6509	Remote Similarity	NPD5175	Approved
0.6495	Remote Similarity	NPD3618	Phase 1
0.6486	Remote Similarity	NPD6882	Approved
0.6486	Remote Similarity	NPD8297	Approved
0.6477	Remote Similarity	NPD4691	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6455	Remote Similarity	NPD4634	Approved
0.6449	Remote Similarity	NPD5141	Approved
0.6444	Remote Similarity	NPD4687	Approved
0.6436	Remote Similarity	NPD6399	Phase 3
0.6421	Remote Similarity	NPD3667	Approved
0.6408	Remote Similarity	NPD5222	Approved
0.6408	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4697	Phase 3
0.6408	Remote Similarity	NPD5221	Approved
0.6404	Remote Similarity	NPD5276	Approved
0.6395	Remote Similarity	NPD7331	Phase 2
0.6389	Remote Similarity	NPD4767	Approved
0.6389	Remote Similarity	NPD4768	Approved
0.6379	Remote Similarity	NPD6059	Approved
0.6379	Remote Similarity	NPD6054	Approved
0.6346	Remote Similarity	NPD5173	Approved
0.6339	Remote Similarity	NPD6053	Discontinued
0.633	Remote Similarity	NPD6614	Approved
0.6327	Remote Similarity	NPD5279	Phase 3
0.6289	Remote Similarity	NPD3668	Phase 3
0.6273	Remote Similarity	NPD5128	Approved
0.6273	Remote Similarity	NPD4729	Approved
0.6273	Remote Similarity	NPD4730	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6264	Remote Similarity	NPD4058	Approved
0.6261	Remote Similarity	NPD7115	Discovery
0.6239	Remote Similarity	NPD6319	Approved
0.6222	Remote Similarity	NPD4243	Approved
0.6218	Remote Similarity	NPD7604	Phase 2
0.6211	Remote Similarity	NPD4695	Discontinued
0.6207	Remote Similarity	NPD6335	Approved
0.6186	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD6016	Approved
0.6174	Remote Similarity	NPD6274	Approved
0.6167	Remote Similarity	NPD7492	Approved
0.6162	Remote Similarity	NPD4623	Approved
0.6162	Remote Similarity	NPD4519	Discontinued
0.6161	Remote Similarity	NPD5250	Approved
0.6161	Remote Similarity	NPD5249	Phase 3
0.6161	Remote Similarity	NPD5169	Approved
0.6161	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5248	Approved
0.6161	Remote Similarity	NPD5251	Approved
0.6161	Remote Similarity	NPD5135	Approved
0.6161	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD7100	Approved
0.614	Remote Similarity	NPD4632	Approved
0.6134	Remote Similarity	NPD5988	Approved
0.6121	Remote Similarity	NPD6317	Approved
0.6116	Remote Similarity	NPD6616	Approved
0.6111	Remote Similarity	NPD5091	Approved
0.6106	Remote Similarity	NPD5217	Approved
0.6106	Remote Similarity	NPD5216	Approved
0.6106	Remote Similarity	NPD5215	Approved
0.6106	Remote Similarity	NPD5127	Approved
0.6087	Remote Similarity	NPD4785	Approved
0.6087	Remote Similarity	NPD4784	Approved
0.6068	Remote Similarity	NPD6314	Approved
0.6068	Remote Similarity	NPD6313	Approved
0.6067	Remote Similarity	NPD5360	Phase 3
0.6067	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7078	Approved
0.6066	Remote Similarity	NPD8293	Discontinued
0.6061	Remote Similarity	NPD1694	Approved
0.6058	Remote Similarity	NPD5282	Discontinued
0.6058	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7900	Approved
0.6058	Remote Similarity	NPD7748	Approved
0.605	Remote Similarity	NPD6908	Approved
0.605	Remote Similarity	NPD6909	Approved
0.6044	Remote Similarity	NPD5777	Approved
0.6036	Remote Similarity	NPD6412	Phase 2
0.6022	Remote Similarity	NPD3702	Approved
0.6016	Remote Similarity	NPD6033	Approved
0.6016	Remote Similarity	NPD7736	Approved
0.5983	Remote Similarity	NPD6009	Approved
0.598	Remote Similarity	NPD6051	Approved
0.598	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5369	Approved
0.5948	Remote Similarity	NPD5167	Approved
0.5922	Remote Similarity	NPD5785	Approved
0.5918	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6435	Approved
0.5917	Remote Similarity	NPD5983	Phase 2
0.5917	Remote Similarity	NPD6291	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