NPASS Compound

Structure

NPC125366 OpenBabel07101718232D 22 25 0 0 1 0 0 0 0 0999 V2000 0.4122 2.3557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1064 -0.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1604 0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4248 1.4036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6526 -1.1445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6763 0.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5186 -0.6445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7866 -0.6445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4608 1.6696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1128 2.1532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3968 1.7679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8605 1.8336 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9640 -0.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6526 0.8555 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2618 1.0246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5186 0.3555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7866 0.3555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2516 0.9678 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2155 -1.2339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 0.8167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8550 1.9382 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 11 1 0 0 0 0 3 17 1 0 0 0 0 4 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 10 11 1 0 0 0 0 11 18 1 1 0 0 0 12 10 1 6 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 6 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 2 1 1 0 0 0 17 18 1 1 0 0 0 18 9 1 6 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.18
Volume:	315.546
LogP:	3.19
LogD:	2.867
LogS:	-4.463
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.645
Synthetic Accessibility Score:	5.032
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.201
MDCK Permeability:	2.293800571351312e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.192
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	63.782012939453125%
Volume Distribution (VD):	0.56
Pgp-substrate:	32.619590759277344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.373
CYP2C19-inhibitor:	0.224
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.563

ADMET: Excretion

Clearance (CL):	10.854
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.583
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.626
Skin Sensitization:	0.932
Carcinogencity:	0.48
Eye Corrosion:	0.034
Eye Irritation:	0.116
Respiratory Toxicity:	0.137

Download Data

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

Natural Product: NPC125366

Natural Product ID:	NPC125366
*Common Name:**	Marrulactone
IUPAC Name:	n.a.
Synonyms:	Marrulactone
Standard InCHIKey:	AKCKRZRPYZPWJE-GCTGDKDVSA-N
Standard InCHI:	InChI=1S/C18H26O4/c1-11-10-12-14-16(2,15(20)21-12)7-5-8-17(14,3)18(11)9-4-6-13(19)22-18/h11-12,14H,4-10H2,1-3H3/t11-,12-,14+,16+,17+,18-/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@H]3[C@](C)(CCC[C@]3(C)[C@]31CCCC(=O)O3)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080254
PubChem CID:	44254165
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO33187	marrubium globosum ssp. libanoticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19650652]

☑ 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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6562	Tissue	Ileum	Mus musculus	Inhibition	>	50.0	%	PMID[506712]

☑ 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 NPC125366 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	411
0.1-0.2	3609
0.2-0.3	9237
0.3-0.4	13723
0.4-0.5	5690
0.5-0.6	5722
0.6-0.7	3440
0.7-0.8	775
0.8-0.85	80
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC134227
0.9189	High Similarity	NPC55508
0.9054	High Similarity	NPC109510
0.8831	High Similarity	NPC143250
0.8554	High Similarity	NPC477441
0.8537	High Similarity	NPC65133
0.8415	Intermediate Similarity	NPC15091
0.8395	Intermediate Similarity	NPC329490
0.8395	Intermediate Similarity	NPC328639
0.8354	Intermediate Similarity	NPC307865
0.8313	Intermediate Similarity	NPC477434
0.8313	Intermediate Similarity	NPC473299
0.8276	Intermediate Similarity	NPC216137
0.8256	Intermediate Similarity	NPC471459
0.8256	Intermediate Similarity	NPC200580
0.8256	Intermediate Similarity	NPC67653
0.8256	Intermediate Similarity	NPC477440
0.8256	Intermediate Similarity	NPC477443
0.8243	Intermediate Similarity	NPC84562
0.8228	Intermediate Similarity	NPC471046
0.8222	Intermediate Similarity	NPC266417
0.8182	Intermediate Similarity	NPC474379
0.8171	Intermediate Similarity	NPC475743
0.8161	Intermediate Similarity	NPC477442
0.8161	Intermediate Similarity	NPC477433
0.8161	Intermediate Similarity	NPC477444
0.8148	Intermediate Similarity	NPC73013
0.814	Intermediate Similarity	NPC236459
0.814	Intermediate Similarity	NPC471221
0.8118	Intermediate Similarity	NPC248216
0.8095	Intermediate Similarity	NPC181871
0.8095	Intermediate Similarity	NPC9060
0.809	Intermediate Similarity	NPC477495
0.8077	Intermediate Similarity	NPC474755
0.8068	Intermediate Similarity	NPC475878
0.8049	Intermediate Similarity	NPC60568
0.8049	Intermediate Similarity	NPC1882
0.8023	Intermediate Similarity	NPC470920
0.8	Intermediate Similarity	NPC477445
0.8	Intermediate Similarity	NPC474572
0.8	Intermediate Similarity	NPC477205
0.7978	Intermediate Similarity	NPC147272
0.7955	Intermediate Similarity	NPC77756
0.7955	Intermediate Similarity	NPC185529
0.7955	Intermediate Similarity	NPC472146
0.7931	Intermediate Similarity	NPC476435
0.7931	Intermediate Similarity	NPC221993
0.7912	Intermediate Similarity	NPC235109
0.7912	Intermediate Similarity	NPC193785
0.7889	Intermediate Similarity	NPC470424
0.7882	Intermediate Similarity	NPC237938
0.7882	Intermediate Similarity	NPC219535
0.7857	Intermediate Similarity	NPC13494
0.7826	Intermediate Similarity	NPC474921
0.7816	Intermediate Similarity	NPC239938
0.7802	Intermediate Similarity	NPC217329
0.7802	Intermediate Similarity	NPC82633
0.7791	Intermediate Similarity	NPC473350
0.7778	Intermediate Similarity	NPC476189
0.7765	Intermediate Similarity	NPC476721
0.7753	Intermediate Similarity	NPC470114
0.775	Intermediate Similarity	NPC96759
0.7742	Intermediate Similarity	NPC472144
0.7738	Intermediate Similarity	NPC476071
0.7738	Intermediate Similarity	NPC280781
0.7738	Intermediate Similarity	NPC58631
0.7738	Intermediate Similarity	NPC48756
0.7727	Intermediate Similarity	NPC473319
0.7727	Intermediate Similarity	NPC131104
0.7727	Intermediate Similarity	NPC476379
0.7727	Intermediate Similarity	NPC3032
0.7717	Intermediate Similarity	NPC475765
0.7717	Intermediate Similarity	NPC256227
0.7717	Intermediate Similarity	NPC163685
0.7717	Intermediate Similarity	NPC475785
0.7711	Intermediate Similarity	NPC201276
0.7711	Intermediate Similarity	NPC477287
0.7711	Intermediate Similarity	NPC474754
0.7711	Intermediate Similarity	NPC80891
0.7703	Intermediate Similarity	NPC306750
0.7701	Intermediate Similarity	NPC120395
0.7701	Intermediate Similarity	NPC476717
0.7701	Intermediate Similarity	NPC472272
0.7701	Intermediate Similarity	NPC83242
0.7692	Intermediate Similarity	NPC309127
0.7692	Intermediate Similarity	NPC295788
0.7692	Intermediate Similarity	NPC247877
0.7684	Intermediate Similarity	NPC471254
0.7674	Intermediate Similarity	NPC471044
0.7674	Intermediate Similarity	NPC473336
0.7667	Intermediate Similarity	NPC52756
0.7667	Intermediate Similarity	NPC474065
0.764	Intermediate Similarity	NPC61688
0.7634	Intermediate Similarity	NPC472145
0.7634	Intermediate Similarity	NPC471241
0.7625	Intermediate Similarity	NPC123122
0.7619	Intermediate Similarity	NPC477851
0.7614	Intermediate Similarity	NPC175293
0.7609	Intermediate Similarity	NPC287354
0.7609	Intermediate Similarity	NPC90014
0.7609	Intermediate Similarity	NPC56369
0.7609	Intermediate Similarity	NPC62407
0.7604	Intermediate Similarity	NPC471253
0.759	Intermediate Similarity	NPC34046
0.759	Intermediate Similarity	NPC80089
0.759	Intermediate Similarity	NPC475725
0.759	Intermediate Similarity	NPC224802
0.759	Intermediate Similarity	NPC171426
0.759	Intermediate Similarity	NPC324700
0.7586	Intermediate Similarity	NPC476715
0.7586	Intermediate Similarity	NPC62572
0.7582	Intermediate Similarity	NPC161035
0.7568	Intermediate Similarity	NPC478126
0.7561	Intermediate Similarity	NPC474020
0.7561	Intermediate Similarity	NPC92489
0.7556	Intermediate Similarity	NPC88337
0.7556	Intermediate Similarity	NPC50443
0.7556	Intermediate Similarity	NPC18536
0.7556	Intermediate Similarity	NPC475776
0.7556	Intermediate Similarity	NPC475211
0.7553	Intermediate Similarity	NPC253995
0.7553	Intermediate Similarity	NPC474724
0.7529	Intermediate Similarity	NPC470154
0.7529	Intermediate Similarity	NPC71541
0.7529	Intermediate Similarity	NPC271572
0.7529	Intermediate Similarity	NPC45256
0.7529	Intermediate Similarity	NPC285480
0.7529	Intermediate Similarity	NPC260977
0.7529	Intermediate Similarity	NPC470156
0.7529	Intermediate Similarity	NPC474870
0.7529	Intermediate Similarity	NPC30443
0.7528	Intermediate Similarity	NPC477614
0.7528	Intermediate Similarity	NPC226491
0.7527	Intermediate Similarity	NPC473964
0.7527	Intermediate Similarity	NPC116683
0.7527	Intermediate Similarity	NPC29410
0.7527	Intermediate Similarity	NPC200054
0.7526	Intermediate Similarity	NPC88469
0.75	Intermediate Similarity	NPC473434
0.75	Intermediate Similarity	NPC471410
0.75	Intermediate Similarity	NPC80700
0.75	Intermediate Similarity	NPC244969
0.75	Intermediate Similarity	NPC471411
0.75	Intermediate Similarity	NPC320144
0.75	Intermediate Similarity	NPC474841
0.75	Intermediate Similarity	NPC478227
0.75	Intermediate Similarity	NPC213528
0.75	Intermediate Similarity	NPC471446
0.75	Intermediate Similarity	NPC476176
0.7474	Intermediate Similarity	NPC267921
0.7473	Intermediate Similarity	NPC470230
0.7473	Intermediate Similarity	NPC476934
0.7471	Intermediate Similarity	NPC51135
0.7471	Intermediate Similarity	NPC101138
0.7471	Intermediate Similarity	NPC97505
0.7471	Intermediate Similarity	NPC25802
0.7471	Intermediate Similarity	NPC475689
0.7471	Intermediate Similarity	NPC82492
0.747	Intermediate Similarity	NPC317913
0.747	Intermediate Similarity	NPC471151
0.747	Intermediate Similarity	NPC207010
0.7447	Intermediate Similarity	NPC473963
0.7447	Intermediate Similarity	NPC472273
0.7447	Intermediate Similarity	NPC96839
0.7444	Intermediate Similarity	NPC472234
0.7444	Intermediate Similarity	NPC472233
0.7442	Intermediate Similarity	NPC477447
0.7442	Intermediate Similarity	NPC289486
0.7442	Intermediate Similarity	NPC477446
0.7442	Intermediate Similarity	NPC477284
0.7442	Intermediate Similarity	NPC61107
0.7442	Intermediate Similarity	NPC121121
0.7442	Intermediate Similarity	NPC470155
0.7439	Intermediate Similarity	NPC159789
0.7436	Intermediate Similarity	NPC41542
0.7436	Intermediate Similarity	NPC328304
0.7436	Intermediate Similarity	NPC329466
0.7423	Intermediate Similarity	NPC473406
0.7419	Intermediate Similarity	NPC305808
0.7419	Intermediate Similarity	NPC98639
0.7412	Intermediate Similarity	NPC471217
0.7412	Intermediate Similarity	NPC472951
0.7412	Intermediate Similarity	NPC475456
0.7412	Intermediate Similarity	NPC472943
0.7412	Intermediate Similarity	NPC261616
0.7412	Intermediate Similarity	NPC471216
0.7396	Intermediate Similarity	NPC39683
0.7396	Intermediate Similarity	NPC475958
0.7381	Intermediate Similarity	NPC185465
0.7381	Intermediate Similarity	NPC472608
0.7381	Intermediate Similarity	NPC243594
0.7381	Intermediate Similarity	NPC31031
0.7374	Intermediate Similarity	NPC126753
0.7368	Intermediate Similarity	NPC89099
0.7368	Intermediate Similarity	NPC476807
0.7368	Intermediate Similarity	NPC476806
0.7368	Intermediate Similarity	NPC471038
0.7368	Intermediate Similarity	NPC28864
0.7368	Intermediate Similarity	NPC20479
0.7368	Intermediate Similarity	NPC38471

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 NPC125366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	3713
0.2-0.3	3280
0.3-0.4	1096
0.4-0.5	284
0.5-0.6	217
0.6-0.7	119
0.7-0.8	18
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.759	Intermediate Similarity	NPD6114	Approved
0.759	Intermediate Similarity	NPD6118	Approved
0.759	Intermediate Similarity	NPD6697	Approved
0.759	Intermediate Similarity	NPD6115	Approved
0.7529	Intermediate Similarity	NPD1779	Approved
0.7529	Intermediate Similarity	NPD1780	Approved
0.747	Intermediate Similarity	NPD6116	Phase 1
0.7439	Intermediate Similarity	NPD3703	Phase 2
0.7439	Intermediate Similarity	NPD3702	Approved
0.7349	Intermediate Similarity	NPD6117	Approved
0.7284	Intermediate Similarity	NPD5777	Approved
0.7273	Intermediate Similarity	NPD6008	Approved
0.7129	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1700	Approved
0.6915	Remote Similarity	NPD8034	Phase 2
0.6915	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3669	Approved
0.6707	Remote Similarity	NPD229	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3573	Approved
0.6598	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7900	Approved
0.6571	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5360	Phase 3
0.6495	Remote Similarity	NPD6399	Phase 3
0.6471	Remote Similarity	NPD6081	Approved
0.6452	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6928	Phase 2
0.6442	Remote Similarity	NPD6675	Approved
0.6442	Remote Similarity	NPD6402	Approved
0.6442	Remote Similarity	NPD7128	Approved
0.6442	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD3698	Phase 2
0.6415	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6372	Approved
0.64	Remote Similarity	NPD7902	Approved
0.6381	Remote Similarity	NPD5701	Approved
0.6381	Remote Similarity	NPD5697	Approved
0.6372	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD2254	Approved
0.6353	Remote Similarity	NPD4244	Approved
0.6353	Remote Similarity	NPD2686	Approved
0.6353	Remote Similarity	NPD4245	Approved
0.6353	Remote Similarity	NPD2687	Approved
0.6341	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7638	Approved
0.633	Remote Similarity	NPD4632	Approved
0.6321	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD6899	Approved
0.6321	Remote Similarity	NPD6881	Approved
0.6321	Remote Similarity	NPD6011	Approved
0.6306	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6649	Approved
0.6296	Remote Similarity	NPD6650	Approved
0.6279	Remote Similarity	NPD4758	Discontinued
0.6275	Remote Similarity	NPD7639	Approved
0.6275	Remote Similarity	NPD7640	Approved
0.6263	Remote Similarity	NPD7748	Approved
0.6262	Remote Similarity	NPD6013	Approved
0.6262	Remote Similarity	NPD6014	Approved
0.6262	Remote Similarity	NPD6012	Approved
0.6222	Remote Similarity	NPD3671	Phase 1
0.6211	Remote Similarity	NPD7334	Approved
0.6211	Remote Similarity	NPD5330	Approved
0.6211	Remote Similarity	NPD6684	Approved
0.6211	Remote Similarity	NPD7146	Approved
0.6211	Remote Similarity	NPD6409	Approved
0.6211	Remote Similarity	NPD7521	Approved
0.6204	Remote Similarity	NPD6883	Approved
0.6204	Remote Similarity	NPD7290	Approved
0.6204	Remote Similarity	NPD7102	Approved
0.6182	Remote Similarity	NPD8133	Approved
0.6163	Remote Similarity	NPD4789	Approved
0.6161	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD7632	Discontinued
0.6147	Remote Similarity	NPD8130	Phase 1
0.6147	Remote Similarity	NPD6617	Approved
0.6147	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6847	Approved
0.6147	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD6319	Approved
0.6117	Remote Similarity	NPD8418	Phase 2
0.6105	Remote Similarity	NPD1694	Approved
0.61	Remote Similarity	NPD6001	Approved
0.6091	Remote Similarity	NPD6882	Approved
0.6091	Remote Similarity	NPD8297	Approved
0.6087	Remote Similarity	NPD5983	Phase 2
0.6082	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6903	Approved
0.6082	Remote Similarity	NPD5737	Approved
0.6082	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD4755	Approved
0.6068	Remote Similarity	NPD7492	Approved
0.6061	Remote Similarity	NPD7515	Phase 2
0.6047	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4238	Approved
0.6044	Remote Similarity	NPD4802	Phase 2
0.6044	Remote Similarity	NPD5364	Discontinued
0.6042	Remote Similarity	NPD3618	Phase 1
0.602	Remote Similarity	NPD5328	Approved
0.6017	Remote Similarity	NPD7507	Approved
0.6017	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6054	Approved
0.5983	Remote Similarity	NPD7604	Phase 2
0.5983	Remote Similarity	NPD8328	Phase 3
0.598	Remote Similarity	NPD4697	Phase 3
0.5966	Remote Similarity	NPD8293	Discontinued
0.5966	Remote Similarity	NPD7078	Approved
0.5962	Remote Similarity	NPD4696	Approved
0.5962	Remote Similarity	NPD4700	Approved
0.5962	Remote Similarity	NPD5286	Approved
0.5962	Remote Similarity	NPD5285	Approved
0.5957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD1810	Approved
0.5955	Remote Similarity	NPD1811	Approved
0.5948	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6016	Approved
0.5948	Remote Similarity	NPD6015	Approved
0.5929	Remote Similarity	NPD6274	Approved
0.5929	Remote Similarity	NPD6940	Discontinued
0.5917	Remote Similarity	NPD7736	Approved
0.5905	Remote Similarity	NPD5223	Approved
0.59	Remote Similarity	NPD6411	Approved
0.59	Remote Similarity	NPD6079	Approved
0.5897	Remote Similarity	NPD6370	Approved
0.5897	Remote Similarity	NPD5988	Approved
0.5882	Remote Similarity	NPD6336	Discontinued
0.5877	Remote Similarity	NPD6317	Approved
0.5876	Remote Similarity	NPD6098	Approved
0.5872	Remote Similarity	NPD6686	Approved
0.5868	Remote Similarity	NPD7319	Approved
0.5865	Remote Similarity	NPD5696	Approved
0.5862	Remote Similarity	NPD3726	Approved
0.5862	Remote Similarity	NPD3725	Approved
0.5859	Remote Similarity	NPD6080	Approved
0.5859	Remote Similarity	NPD6673	Approved
0.5859	Remote Similarity	NPD6904	Approved
0.5849	Remote Similarity	NPD5226	Approved
0.5849	Remote Similarity	NPD4633	Approved
0.5849	Remote Similarity	NPD5211	Phase 2
0.5849	Remote Similarity	NPD5225	Approved
0.5849	Remote Similarity	NPD5224	Approved
0.5842	Remote Similarity	NPD8171	Discontinued
0.5842	Remote Similarity	NPD4202	Approved
0.5833	Remote Similarity	NPD371	Approved
0.5833	Remote Similarity	NPD3668	Phase 3
0.5826	Remote Similarity	NPD6313	Approved
0.5826	Remote Similarity	NPD6335	Approved
0.5826	Remote Similarity	NPD6314	Approved
0.5825	Remote Similarity	NPD5222	Approved
0.5825	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5221	Approved
0.58	Remote Similarity	NPD5207	Approved
0.5794	Remote Similarity	NPD5175	Approved
0.5794	Remote Similarity	NPD4754	Approved
0.5794	Remote Similarity	NPD5174	Approved
0.5789	Remote Similarity	NPD3667	Approved
0.578	Remote Similarity	NPD6412	Phase 2
0.5776	Remote Similarity	NPD7100	Approved
0.5776	Remote Similarity	NPD7101	Approved
0.5769	Remote Similarity	NPD5173	Approved
0.5769	Remote Similarity	NPD6083	Phase 2
0.5769	Remote Similarity	NPD6084	Phase 2
0.5766	Remote Similarity	NPD4634	Approved
0.5758	Remote Similarity	NPD5208	Approved
0.5743	Remote Similarity	NPD5693	Phase 1
0.5741	Remote Similarity	NPD5141	Approved
0.5728	Remote Similarity	NPD5695	Phase 3
0.5728	Remote Similarity	NPD7991	Discontinued
0.5714	Remote Similarity	NPD4225	Approved
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6101	Approved
0.5696	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4768	Approved
0.5688	Remote Similarity	NPD4767	Approved
0.5678	Remote Similarity	NPD6908	Approved
0.5678	Remote Similarity	NPD6909	Approved
0.567	Remote Similarity	NPD4786	Approved
0.5656	Remote Similarity	NPD6033	Approved
0.5652	Remote Similarity	NPD6868	Approved
0.5647	Remote Similarity	NPD7909	Approved
0.5644	Remote Similarity	NPD5692	Phase 3
0.5631	Remote Similarity	NPD5282	Discontinued

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