NPASS Compound

Structure

NPC469323 OpenBabel07101718222D 33 38 0 0 1 0 0 0 0 0999 V2000 0.7503 -2.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8881 2.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8625 2.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6140 -0.7884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8257 -0.2157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 0.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2920 -2.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3230 -2.1656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8647 -1.4791 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4994 -0.4872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 -1.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8337 -1.5810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7239 -1.1847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 2 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 -5.0629 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4684 -0.5890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6220 -2.1537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 0 0 0 0 17 1 1 1 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 20 32 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 0 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 25 27 1 0 0 0 0 25 33 1 6 0 0 0 27 33 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.15
Volume:	310.707
LogP:	0.482
LogD:	0.925
LogS:	-1.695
# Rotatable Bonds:	3
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.544
Synthetic Accessibility Score:	4.569
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.003
MDCK Permeability:	1.0847301382455043e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.817
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.491
Plasma Protein Binding (PPB):	86.43098449707031%
Volume Distribution (VD):	0.932
Pgp-substrate:	13.024542808532715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.682
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.524
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	5.963
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.266
Skin Sensitization:	0.088
Carcinogencity:	0.575
Eye Corrosion:	0.006
Eye Irritation:	0.053
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC469323

Natural Product ID:	NPC469323
*Common Name:**	TURRMTUNTOXXAR-PCIVBCIOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TURRMTUNTOXXAR-PCIVBCIOSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-17-15-19(25-27(4,5)33-25)32-20-16-30(8)18(24(17)20)9-10-22-28(6)13-12-23(31)26(2,3)21(28)11-14-29(22,30)7/h17,19-22,25H,9-16H2,1-8H3/t17-,19?,20?,21?,22?,25-,28+,29+,30+/m1/s1
SMILES:	CC1CC(OC2C1=C3CCC4C5(CCC(=O)C(C5CCC4(C3(C2)C)C)(C)C)C)C6C(O6)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL105315
PubChem CID:	44335328
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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-5.1	%	PMID[515680]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	21.7	%	PMID[515680]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	31.2	%	PMID[515680]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	84.2	%	PMID[515680]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	100.4	%	PMID[515680]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	12000.0	nM	PMID[515680]

☑ 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 NPC469323 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	267
0.1-0.2	1819
0.2-0.3	6255
0.3-0.4	16211
0.4-0.5	6904
0.5-0.6	7365
0.6-0.7	3683
0.7-0.8	182
0.8-0.85	5
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.871	High Similarity	NPC303777
0.871	High Similarity	NPC471784
0.8636	High Similarity	NPC469322
0.8351	Intermediate Similarity	NPC324001
0.8333	Intermediate Similarity	NPC473174
0.8229	Intermediate Similarity	NPC473176
0.8172	Intermediate Similarity	NPC274046
0.8172	Intermediate Similarity	NPC198074
0.8081	Intermediate Similarity	NPC473175
0.7979	Intermediate Similarity	NPC469315
0.7978	Intermediate Similarity	NPC470047
0.7978	Intermediate Similarity	NPC470046
0.7978	Intermediate Similarity	NPC86370
0.7917	Intermediate Similarity	NPC471777
0.7912	Intermediate Similarity	NPC470051
0.7912	Intermediate Similarity	NPC470050
0.7879	Intermediate Similarity	NPC469316
0.7872	Intermediate Similarity	NPC262870
0.7872	Intermediate Similarity	NPC473166
0.7835	Intermediate Similarity	NPC151488
0.7802	Intermediate Similarity	NPC137493
0.7778	Intermediate Similarity	NPC476897
0.7745	Intermediate Similarity	NPC473173
0.7745	Intermediate Similarity	NPC469318
0.7745	Intermediate Similarity	NPC144459
0.7732	Intermediate Similarity	NPC471822
0.7708	Intermediate Similarity	NPC67831
0.7708	Intermediate Similarity	NPC174051
0.77	Intermediate Similarity	NPC185530
0.7634	Intermediate Similarity	NPC469317
0.7634	Intermediate Similarity	NPC469314
0.7634	Intermediate Similarity	NPC241875
0.7629	Intermediate Similarity	NPC469329
0.7629	Intermediate Similarity	NPC473415
0.7629	Intermediate Similarity	NPC30677
0.7629	Intermediate Similarity	NPC37787
0.7629	Intermediate Similarity	NPC180557
0.7624	Intermediate Similarity	NPC26478
0.7609	Intermediate Similarity	NPC470048
0.7604	Intermediate Similarity	NPC141447
0.76	Intermediate Similarity	NPC469327
0.7579	Intermediate Similarity	NPC161638
0.7576	Intermediate Similarity	NPC471582
0.7573	Intermediate Similarity	NPC473165
0.7573	Intermediate Similarity	NPC471601
0.7573	Intermediate Similarity	NPC9457
0.7573	Intermediate Similarity	NPC471783
0.7526	Intermediate Similarity	NPC318332
0.75	Intermediate Similarity	NPC190442
0.75	Intermediate Similarity	NPC49420
0.75	Intermediate Similarity	NPC473157
0.75	Intermediate Similarity	NPC109512
0.7476	Intermediate Similarity	NPC60681
0.7423	Intermediate Similarity	NPC169343
0.7423	Intermediate Similarity	NPC229976
0.7407	Intermediate Similarity	NPC284915
0.7404	Intermediate Similarity	NPC473169
0.7396	Intermediate Similarity	NPC198818
0.7396	Intermediate Similarity	NPC8062
0.7396	Intermediate Similarity	NPC472307
0.7391	Intermediate Similarity	NPC170862
0.7383	Intermediate Similarity	NPC476163
0.7379	Intermediate Similarity	NPC75531
0.7379	Intermediate Similarity	NPC149124
0.7374	Intermediate Similarity	NPC160056
0.7347	Intermediate Similarity	NPC240617
0.734	Intermediate Similarity	NPC471737
0.734	Intermediate Similarity	NPC195640
0.7333	Intermediate Similarity	NPC61411
0.7333	Intermediate Similarity	NPC177064
0.7308	Intermediate Similarity	NPC470587
0.7303	Intermediate Similarity	NPC470750
0.7303	Intermediate Similarity	NPC470557
0.7292	Intermediate Similarity	NPC229871
0.7292	Intermediate Similarity	NPC285982
0.7292	Intermediate Similarity	NPC2983
0.7292	Intermediate Similarity	NPC469319
0.7283	Intermediate Similarity	NPC163236
0.7282	Intermediate Similarity	NPC239716
0.7273	Intermediate Similarity	NPC312824
0.7273	Intermediate Similarity	NPC33473
0.7273	Intermediate Similarity	NPC470493
0.7273	Intermediate Similarity	NPC183580
0.7263	Intermediate Similarity	NPC477228
0.7263	Intermediate Similarity	NPC90652
0.7255	Intermediate Similarity	NPC474327
0.7245	Intermediate Similarity	NPC475700
0.7241	Intermediate Similarity	NPC474123
0.7238	Intermediate Similarity	NPC131665
0.7238	Intermediate Similarity	NPC255387
0.7234	Intermediate Similarity	NPC471224
0.7234	Intermediate Similarity	NPC274724
0.7234	Intermediate Similarity	NPC323765
0.7222	Intermediate Similarity	NPC470052
0.7216	Intermediate Similarity	NPC320026
0.7216	Intermediate Similarity	NPC76286
0.7207	Intermediate Similarity	NPC113448
0.7204	Intermediate Similarity	NPC472744
0.72	Intermediate Similarity	NPC472362
0.72	Intermediate Similarity	NPC322063
0.72	Intermediate Similarity	NPC472363
0.72	Intermediate Similarity	NPC154526
0.7196	Intermediate Similarity	NPC29133
0.7191	Intermediate Similarity	NPC198473
0.7188	Intermediate Similarity	NPC474845
0.7188	Intermediate Similarity	NPC478261
0.7188	Intermediate Similarity	NPC478259
0.7188	Intermediate Similarity	NPC478260
0.7188	Intermediate Similarity	NPC28227
0.7188	Intermediate Similarity	NPC470417
0.7174	Intermediate Similarity	NPC282293
0.7172	Intermediate Similarity	NPC84893
0.7158	Intermediate Similarity	NPC469994
0.7158	Intermediate Similarity	NPC472505
0.7157	Intermediate Similarity	NPC83709
0.7143	Intermediate Similarity	NPC264954
0.7143	Intermediate Similarity	NPC218301
0.7143	Intermediate Similarity	NPC473167
0.7143	Intermediate Similarity	NPC215843
0.7143	Intermediate Similarity	NPC476177
0.7143	Intermediate Similarity	NPC42673
0.713	Intermediate Similarity	NPC470960
0.713	Intermediate Similarity	NPC470961
0.7129	Intermediate Similarity	NPC121402
0.7129	Intermediate Similarity	NPC10057
0.7129	Intermediate Similarity	NPC151681
0.7129	Intermediate Similarity	NPC132753
0.7129	Intermediate Similarity	NPC76266
0.7129	Intermediate Similarity	NPC175351
0.7129	Intermediate Similarity	NPC224356
0.7129	Intermediate Similarity	NPC110937
0.7129	Intermediate Similarity	NPC2049
0.7128	Intermediate Similarity	NPC475193
0.7128	Intermediate Similarity	NPC312660
0.7128	Intermediate Similarity	NPC82902
0.7128	Intermediate Similarity	NPC227132
0.7128	Intermediate Similarity	NPC120158
0.7117	Intermediate Similarity	NPC167606
0.7117	Intermediate Similarity	NPC286528
0.7117	Intermediate Similarity	NPC20302
0.7117	Intermediate Similarity	NPC470492
0.7117	Intermediate Similarity	NPC140055
0.7115	Intermediate Similarity	NPC112009
0.7115	Intermediate Similarity	NPC180204
0.7115	Intermediate Similarity	NPC470954
0.7115	Intermediate Similarity	NPC168575
0.7113	Intermediate Similarity	NPC122116
0.7111	Intermediate Similarity	NPC316500
0.71	Intermediate Similarity	NPC280877
0.71	Intermediate Similarity	NPC84383
0.7097	Intermediate Similarity	NPC477858
0.7097	Intermediate Similarity	NPC145143
0.7097	Intermediate Similarity	NPC469325
0.7087	Intermediate Similarity	NPC471075
0.7087	Intermediate Similarity	NPC310981
0.7087	Intermediate Similarity	NPC476888
0.7087	Intermediate Similarity	NPC93744
0.7087	Intermediate Similarity	NPC235142
0.7083	Intermediate Similarity	NPC317590
0.708	Intermediate Similarity	NPC251226
0.708	Intermediate Similarity	NPC154491
0.708	Intermediate Similarity	NPC268530
0.708	Intermediate Similarity	NPC474370
0.7079	Intermediate Similarity	NPC475771
0.7079	Intermediate Similarity	NPC469678
0.7079	Intermediate Similarity	NPC469669
0.7075	Intermediate Similarity	NPC180744
0.7065	Intermediate Similarity	NPC267517
0.7065	Intermediate Similarity	NPC233332
0.7064	Intermediate Similarity	NPC191620
0.7064	Intermediate Similarity	NPC470063
0.7059	Intermediate Similarity	NPC98868
0.7059	Intermediate Similarity	NPC234617
0.7059	Intermediate Similarity	NPC124703
0.7054	Intermediate Similarity	NPC473720
0.7054	Intermediate Similarity	NPC709
0.7054	Intermediate Similarity	NPC50774
0.7054	Intermediate Similarity	NPC186525
0.7053	Intermediate Similarity	NPC474083
0.7053	Intermediate Similarity	NPC474218
0.7053	Intermediate Similarity	NPC476678
0.7053	Intermediate Similarity	NPC470223
0.7053	Intermediate Similarity	NPC189311
0.7045	Intermediate Similarity	NPC107783
0.7045	Intermediate Similarity	NPC92909
0.7041	Intermediate Similarity	NPC273199
0.7041	Intermediate Similarity	NPC478257
0.7041	Intermediate Similarity	NPC219495
0.7041	Intermediate Similarity	NPC478258
0.7041	Intermediate Similarity	NPC113393
0.7041	Intermediate Similarity	NPC101651
0.7041	Intermediate Similarity	NPC171441
0.7041	Intermediate Similarity	NPC85173
0.7041	Intermediate Similarity	NPC159748
0.7037	Intermediate Similarity	NPC472215
0.7037	Intermediate Similarity	NPC472214
0.7037	Intermediate Similarity	NPC253906
0.7033	Intermediate Similarity	NPC63020
0.703	Intermediate Similarity	NPC471775
0.7027	Intermediate Similarity	NPC268213

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 NPC469323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	2169
0.2-0.3	4096
0.3-0.4	1883
0.4-0.5	415
0.5-0.6	262
0.6-0.7	86
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
0.7553	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.7188	Intermediate Similarity	NPD6903	Approved
0.7117	Intermediate Similarity	NPD7115	Discovery
0.7075	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6098	Approved
0.697	Remote Similarity	NPD5693	Phase 1
0.6947	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD3666	Approved
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6944	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6051	Approved
0.6932	Remote Similarity	NPD5777	Approved
0.6916	Remote Similarity	NPD6412	Phase 2
0.6915	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3667	Approved
0.6881	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4788	Approved
0.6837	Remote Similarity	NPD6672	Approved
0.6837	Remote Similarity	NPD5737	Approved
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD6083	Phase 2
0.6771	Remote Similarity	NPD3668	Phase 3
0.6768	Remote Similarity	NPD6904	Approved
0.6768	Remote Similarity	NPD4753	Phase 2
0.6768	Remote Similarity	NPD6080	Approved
0.6768	Remote Similarity	NPD6673	Approved
0.6765	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4221	Approved
0.6737	Remote Similarity	NPD4223	Phase 3
0.6733	Remote Similarity	NPD6399	Phase 3
0.6731	Remote Similarity	NPD7638	Approved
0.6701	Remote Similarity	NPD5329	Approved
0.6701	Remote Similarity	NPD1694	Approved
0.6697	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6633	Remote Similarity	NPD3618	Phase 1
0.6633	Remote Similarity	NPD4519	Discontinued
0.6633	Remote Similarity	NPD4623	Approved
0.6632	Remote Similarity	NPD4692	Approved
0.6632	Remote Similarity	NPD4139	Approved
0.6629	Remote Similarity	NPD4245	Approved
0.6629	Remote Similarity	NPD4244	Approved
0.6604	Remote Similarity	NPD4159	Approved
0.6602	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD5328	Approved
0.6598	Remote Similarity	NPD4197	Approved
0.6571	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD4202	Approved
0.6566	Remote Similarity	NPD3573	Approved
0.6542	Remote Similarity	NPD7632	Discontinued
0.6531	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3698	Phase 2
0.6514	Remote Similarity	NPD6675	Approved
0.6514	Remote Similarity	NPD6008	Approved
0.6514	Remote Similarity	NPD6402	Approved
0.6514	Remote Similarity	NPD7128	Approved
0.6514	Remote Similarity	NPD5739	Approved
0.6505	Remote Similarity	NPD6001	Approved
0.6476	Remote Similarity	NPD4755	Approved
0.6476	Remote Similarity	NPD7902	Approved
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD6050	Approved
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD7515	Phase 2
0.6471	Remote Similarity	NPD6079	Approved
0.6465	Remote Similarity	NPD4690	Approved
0.6465	Remote Similarity	NPD4138	Approved
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5205	Approved
0.6465	Remote Similarity	NPD4693	Phase 3
0.6465	Remote Similarity	NPD4688	Approved
0.6465	Remote Similarity	NPD4689	Approved
0.646	Remote Similarity	NPD8297	Approved
0.6442	Remote Similarity	NPD4629	Approved
0.6442	Remote Similarity	NPD5210	Approved
0.6404	Remote Similarity	NPD8133	Approved
0.6396	Remote Similarity	NPD7320	Approved
0.6396	Remote Similarity	NPD6899	Approved
0.6396	Remote Similarity	NPD6881	Approved
0.6389	Remote Similarity	NPD5211	Phase 2
0.6374	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5692	Phase 3
0.6373	Remote Similarity	NPD5207	Approved
0.6355	Remote Similarity	NPD5286	Approved
0.6355	Remote Similarity	NPD4700	Approved
0.6355	Remote Similarity	NPD5285	Approved
0.6355	Remote Similarity	NPD4696	Approved
0.6344	Remote Similarity	NPD3702	Approved
0.6339	Remote Similarity	NPD6373	Approved
0.6339	Remote Similarity	NPD6372	Approved
0.6339	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4137	Phase 3
0.6333	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7327	Approved
0.6325	Remote Similarity	NPD7328	Approved
0.6311	Remote Similarity	NPD5694	Approved
0.6306	Remote Similarity	NPD5701	Approved
0.6306	Remote Similarity	NPD5697	Approved
0.63	Remote Similarity	NPD5280	Approved
0.63	Remote Similarity	NPD4694	Approved
0.63	Remote Similarity	NPD5690	Phase 2
0.63	Remote Similarity	NPD5279	Phase 3
0.6283	Remote Similarity	NPD7290	Approved
0.6283	Remote Similarity	NPD6883	Approved
0.6283	Remote Similarity	NPD7102	Approved
0.6273	Remote Similarity	NPD5141	Approved
0.6271	Remote Similarity	NPD7516	Approved
0.6264	Remote Similarity	NPD4789	Approved
0.6264	Remote Similarity	NPD4691	Approved
0.6264	Remote Similarity	NPD4747	Approved
0.6262	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD5225	Approved
0.6239	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD5224	Approved
0.6228	Remote Similarity	NPD6617	Approved
0.6228	Remote Similarity	NPD6650	Approved
0.6228	Remote Similarity	NPD8130	Phase 1
0.6228	Remote Similarity	NPD6649	Approved
0.6228	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD6847	Approved
0.6222	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5360	Phase 3
0.6218	Remote Similarity	NPD8377	Approved
0.6218	Remote Similarity	NPD8294	Approved
0.6214	Remote Similarity	NPD6698	Approved
0.6214	Remote Similarity	NPD46	Approved
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.6186	Remote Similarity	NPD7525	Registered
0.6182	Remote Similarity	NPD5174	Approved
0.6182	Remote Similarity	NPD5175	Approved
0.6174	Remote Similarity	NPD6882	Approved
0.617	Remote Similarity	NPD8039	Approved
0.6168	Remote Similarity	NPD5959	Approved
0.6167	Remote Similarity	NPD8296	Approved
0.6167	Remote Similarity	NPD8335	Approved
0.6167	Remote Similarity	NPD8380	Approved
0.6167	Remote Similarity	NPD8379	Approved
0.6167	Remote Similarity	NPD8033	Approved
0.6167	Remote Similarity	NPD8378	Approved
0.6147	Remote Similarity	NPD5223	Approved
0.614	Remote Similarity	NPD6371	Approved
0.6132	Remote Similarity	NPD5654	Approved
0.6121	Remote Similarity	NPD7094	Approved
0.6121	Remote Similarity	NPD6858	Approved
0.6117	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD1695	Approved
0.6106	Remote Similarity	NPD6011	Approved
0.6105	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5133	Approved
0.6087	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6054	Approved
0.6083	Remote Similarity	NPD6059	Approved
0.6082	Remote Similarity	NPD4195	Approved
0.6078	Remote Similarity	NPD7524	Approved
0.6075	Remote Similarity	NPD7732	Phase 3
0.6075	Remote Similarity	NPD5221	Approved
0.6075	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5222	Approved
0.6075	Remote Similarity	NPD4697	Phase 3
0.6071	Remote Similarity	NPD4767	Approved
0.6071	Remote Similarity	NPD4768	Approved
0.6067	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5733	Approved
0.6064	Remote Similarity	NPD4058	Approved
0.6061	Remote Similarity	NPD5209	Approved
0.604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6052	Approved
0.6036	Remote Similarity	NPD4754	Approved
0.6034	Remote Similarity	NPD6053	Discontinued
0.6033	Remote Similarity	NPD7503	Approved
0.6022	Remote Similarity	NPD4243	Approved
0.602	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD6695	Phase 3

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