NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	744.25
Volume:	679.181
LogP:	-0.119
LogD:	-0.283
LogS:	-2.802
# Rotatable Bonds:	10
TPSA:	297.89
# H-Bond Aceptor:	19
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	6.154
Fsp3:	0.727
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.708
MDCK Permeability:	0.0001793066185200587
Pgp-inhibitor:	0.004
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.948
20% Bioavailability (F20%):	0.143
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	32.2084846496582%
Volume Distribution (VD):	0.42
Pgp-substrate:	29.953510284423828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	1.006
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.314
Human Hepatotoxicity (H-HT):	0.532
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.292
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.105

Download Data

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

Natural Product: NPC477735

Natural Product ID:	NPC477735
*Common Name:**	phyllaemblicin B
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (2S,3aR,4R,4'S,5'R,6S,7aR)-4'-benzoyloxy-3a,4-dihydroxy-5'-methyl-3-oxospiro[5,6,7,7a-tetrahydro-4H-1-benzofuran-2,2'-oxane]-6-carboxylate
Synonyms:
Standard InCHIKey:	RLZZBHBWPWGOSA-MYVHNFIBSA-N
Standard InCHI:	InChI=1S/C33H44O19/c1-13-12-46-32(9-16(13)47-27(42)14-5-3-2-4-6-14)31(44)33(45)19(36)7-15(8-20(33)52-32)28(43)51-30-26(24(40)22(38)18(11-35)49-30)50-29-25(41)23(39)21(37)17(10-34)48-29/h2-6,13,15-26,29-30,34-41,45H,7-12H2,1H3/t13-,15+,16+,17-,18-,19-,20-,21-,22-,23+,24+,25-,26-,29+,30+,32+,33-/m1/s1
SMILES:	C[C@@H]1CO[C@]2(C[C@@H]1OC(=O)C3=CC=CC=C3)C(=O)[C@]4([C@@H](C[C@@H](C[C@H]4O2)C(=O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45269660
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754604]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	Roots	Simao city, Yunnan Province, China	2007-MAY	PMID[19374435]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	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
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	50.2	ug/ml	PMID[19374435]
NPT3494	Organism	Coxsackievirus	Coxsackievirus	IC50	=	7.8	ug/ml	PMID[19374435]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	6.4	n.a.	PMID[19374435]

☑ 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 NPC477735 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	345
0.1-0.2	1215
0.2-0.3	2689
0.3-0.4	5620
0.4-0.5	10208
0.5-0.6	10834
0.6-0.7	8918
0.7-0.8	2531
0.8-0.85	252
0.85-0.9	72
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC477736
0.9384	High Similarity	NPC477737
0.9295	High Similarity	NPC102465
0.9161	High Similarity	NPC150893
0.9161	High Similarity	NPC329960
0.9161	High Similarity	NPC295408
0.9114	High Similarity	NPC477473
0.9114	High Similarity	NPC477466
0.9114	High Similarity	NPC477469
0.9114	High Similarity	NPC477471
0.8912	High Similarity	NPC77493
0.8861	High Similarity	NPC471493
0.8839	High Similarity	NPC469417
0.8831	High Similarity	NPC472549
0.8812	High Similarity	NPC469420
0.8797	High Similarity	NPC66193
0.8782	High Similarity	NPC469399
0.8774	High Similarity	NPC106895
0.8766	High Similarity	NPC469477
0.8766	High Similarity	NPC133430
0.8758	High Similarity	NPC51602
0.8758	High Similarity	NPC471103
0.8742	High Similarity	NPC471134
0.8734	High Similarity	NPC43304
0.8734	High Similarity	NPC477188
0.8734	High Similarity	NPC477190
0.8726	High Similarity	NPC477623
0.8712	High Similarity	NPC469421
0.871	High Similarity	NPC282239
0.871	High Similarity	NPC5115
0.871	High Similarity	NPC21410
0.871	High Similarity	NPC473670
0.8701	High Similarity	NPC477905
0.8701	High Similarity	NPC472548
0.8693	High Similarity	NPC7095
0.8688	High Similarity	NPC61891
0.8662	High Similarity	NPC477467
0.8662	High Similarity	NPC471102
0.8654	High Similarity	NPC217091
0.8645	High Similarity	NPC472022
0.8645	High Similarity	NPC304876
0.8645	High Similarity	NPC472005
0.8645	High Similarity	NPC472030
0.8645	High Similarity	NPC473414
0.8645	High Similarity	NPC237549
0.8645	High Similarity	NPC1173
0.8645	High Similarity	NPC257213
0.8645	High Similarity	NPC69425
0.8645	High Similarity	NPC242262
0.8645	High Similarity	NPC158333
0.8645	High Similarity	NPC249471
0.8645	High Similarity	NPC265395
0.8645	High Similarity	NPC256142
0.8642	High Similarity	NPC477488
0.8627	High Similarity	NPC60509
0.8627	High Similarity	NPC250046
0.8627	High Similarity	NPC81698
0.8599	High Similarity	NPC477474
0.8599	High Similarity	NPC477472
0.8599	High Similarity	NPC472393
0.8599	High Similarity	NPC477470
0.859	High Similarity	NPC112523
0.859	High Similarity	NPC469398
0.859	High Similarity	NPC26033
0.859	High Similarity	NPC228204
0.859	High Similarity	NPC114410
0.858	High Similarity	NPC40138
0.8571	High Similarity	NPC112216
0.8571	High Similarity	NPC161239
0.8571	High Similarity	NPC477491
0.8571	High Similarity	NPC165260
0.8571	High Similarity	NPC198455
0.8562	High Similarity	NPC322420
0.8553	High Similarity	NPC127857
0.8544	High Similarity	NPC49297
0.8544	High Similarity	NPC476784
0.8526	High Similarity	NPC77719
0.8516	High Similarity	NPC306799
0.8516	High Similarity	NPC101043
0.8516	High Similarity	NPC329657
0.85	High Similarity	NPC275477
0.8497	Intermediate Similarity	NPC469513
0.8481	Intermediate Similarity	NPC469771
0.8481	Intermediate Similarity	NPC181924
0.8471	Intermediate Similarity	NPC469422
0.8457	Intermediate Similarity	NPC325732
0.8457	Intermediate Similarity	NPC324769
0.8452	Intermediate Similarity	NPC470245
0.8452	Intermediate Similarity	NPC473214
0.8452	Intermediate Similarity	NPC469448
0.8452	Intermediate Similarity	NPC254558
0.8431	Intermediate Similarity	NPC471107
0.8431	Intermediate Similarity	NPC471100
0.8408	Intermediate Similarity	NPC219419
0.8397	Intermediate Similarity	NPC469415
0.8397	Intermediate Similarity	NPC470153
0.8387	Intermediate Similarity	NPC476975
0.8387	Intermediate Similarity	NPC473215
0.8385	Intermediate Similarity	NPC165234
0.8385	Intermediate Similarity	NPC475536
0.8355	Intermediate Similarity	NPC182869
0.8354	Intermediate Similarity	NPC155329
0.8354	Intermediate Similarity	NPC34066
0.8354	Intermediate Similarity	NPC114357
0.8354	Intermediate Similarity	NPC259144
0.8354	Intermediate Similarity	NPC251139
0.8344	Intermediate Similarity	NPC473468
0.8344	Intermediate Similarity	NPC475567
0.8344	Intermediate Similarity	NPC473557
0.8343	Intermediate Similarity	NPC470581
0.8343	Intermediate Similarity	NPC470582
0.8343	Intermediate Similarity	NPC115447
0.8333	Intermediate Similarity	NPC473641
0.8333	Intermediate Similarity	NPC303429
0.8333	Intermediate Similarity	NPC475437
0.8333	Intermediate Similarity	NPC475300
0.8333	Intermediate Similarity	NPC222102
0.8333	Intermediate Similarity	NPC475464
0.8333	Intermediate Similarity	NPC475505
0.8333	Intermediate Similarity	NPC473797
0.8323	Intermediate Similarity	NPC183441
0.8313	Intermediate Similarity	NPC319404
0.8312	Intermediate Similarity	NPC277053
0.8312	Intermediate Similarity	NPC301946
0.8303	Intermediate Similarity	NPC469419
0.8294	Intermediate Similarity	NPC283980
0.8294	Intermediate Similarity	NPC187441
0.8293	Intermediate Similarity	NPC475198
0.8293	Intermediate Similarity	NPC475531
0.8293	Intermediate Similarity	NPC475175
0.8291	Intermediate Similarity	NPC11588
0.8291	Intermediate Similarity	NPC248265
0.8291	Intermediate Similarity	NPC146310
0.8291	Intermediate Similarity	NPC134685
0.8291	Intermediate Similarity	NPC229545
0.8284	Intermediate Similarity	NPC176246
0.8282	Intermediate Similarity	NPC477627
0.8247	Intermediate Similarity	NPC80895
0.8247	Intermediate Similarity	NPC471912
0.8239	Intermediate Similarity	NPC473611
0.8239	Intermediate Similarity	NPC132599
0.8239	Intermediate Similarity	NPC469730
0.8239	Intermediate Similarity	NPC469456
0.8239	Intermediate Similarity	NPC473632
0.8235	Intermediate Similarity	NPC472546
0.8235	Intermediate Similarity	NPC83331
0.8235	Intermediate Similarity	NPC266513
0.8225	Intermediate Similarity	NPC470583
0.8225	Intermediate Similarity	NPC19056
0.8224	Intermediate Similarity	NPC183270
0.8224	Intermediate Similarity	NPC477904
0.8221	Intermediate Similarity	NPC478073
0.8217	Intermediate Similarity	NPC91730
0.8214	Intermediate Similarity	NPC477617
0.8214	Intermediate Similarity	NPC270027
0.8194	Intermediate Similarity	NPC177940
0.8194	Intermediate Similarity	NPC469349
0.8194	Intermediate Similarity	NPC473088
0.8194	Intermediate Similarity	NPC184817
0.8194	Intermediate Similarity	NPC29704
0.8194	Intermediate Similarity	NPC200471
0.8194	Intermediate Similarity	NPC472572
0.8194	Intermediate Similarity	NPC472575
0.8194	Intermediate Similarity	NPC470159
0.8194	Intermediate Similarity	NPC70403
0.8194	Intermediate Similarity	NPC96903
0.8194	Intermediate Similarity	NPC472568
0.8194	Intermediate Similarity	NPC470157
0.8194	Intermediate Similarity	NPC174982
0.8194	Intermediate Similarity	NPC171525
0.8194	Intermediate Similarity	NPC476973
0.8194	Intermediate Similarity	NPC158663
0.8194	Intermediate Similarity	NPC471104
0.8194	Intermediate Similarity	NPC472571
0.8187	Intermediate Similarity	NPC154675
0.8187	Intermediate Similarity	NPC11410
0.8176	Intermediate Similarity	NPC469519
0.8176	Intermediate Similarity	NPC472658
0.8176	Intermediate Similarity	NPC471135
0.8176	Intermediate Similarity	NPC472657
0.817	Intermediate Similarity	NPC213567
0.817	Intermediate Similarity	NPC97947
0.817	Intermediate Similarity	NPC41481
0.817	Intermediate Similarity	NPC27377
0.817	Intermediate Similarity	NPC87448
0.817	Intermediate Similarity	NPC472576
0.817	Intermediate Similarity	NPC291599
0.817	Intermediate Similarity	NPC118080
0.817	Intermediate Similarity	NPC16912
0.8166	Intermediate Similarity	NPC65118
0.8165	Intermediate Similarity	NPC197037
0.8163	Intermediate Similarity	NPC226101
0.8163	Intermediate Similarity	NPC301857
0.8163	Intermediate Similarity	NPC237182
0.8161	Intermediate Similarity	NPC294863
0.8161	Intermediate Similarity	NPC282636
0.816	Intermediate Similarity	NPC478124
0.8153	Intermediate Similarity	NPC270590
0.8153	Intermediate Similarity	NPC301556
0.8153	Intermediate Similarity	NPC471101

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 NPC477735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	775
0.2-0.3	1720
0.3-0.4	3090
0.4-0.5	2169
0.5-0.6	874
0.6-0.7	192
0.7-0.8	44
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8253	Intermediate Similarity	NPD7799	Discontinued
0.8188	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD8407	Phase 2
0.8059	Intermediate Similarity	NPD8368	Discontinued
0.7853	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7251	Discontinued
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7676	Intermediate Similarity	NPD8319	Approved
0.7676	Intermediate Similarity	NPD8320	Phase 1
0.764	Intermediate Similarity	NPD8435	Approved
0.763	Intermediate Similarity	NPD7074	Phase 3
0.7627	Intermediate Similarity	NPD8434	Phase 2
0.7625	Intermediate Similarity	NPD7236	Approved
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8312	Approved
0.7557	Intermediate Similarity	NPD8313	Approved
0.7542	Intermediate Similarity	NPD8361	Approved
0.7542	Intermediate Similarity	NPD8360	Approved
0.7531	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD7239	Suspended
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7054	Approved
0.7459	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7699	Phase 2
0.7446	Intermediate Similarity	NPD7700	Phase 2
0.743	Intermediate Similarity	NPD8150	Discontinued
0.743	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3818	Discontinued
0.7381	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7075	Discontinued
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.734	Intermediate Similarity	NPD7435	Discontinued
0.7297	Intermediate Similarity	NPD8485	Approved
0.7288	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6535	Approved
0.7283	Intermediate Similarity	NPD6534	Approved
0.7247	Intermediate Similarity	NPD6559	Discontinued
0.7239	Intermediate Similarity	NPD6190	Approved
0.7216	Intermediate Similarity	NPD7228	Approved
0.7205	Intermediate Similarity	NPD7266	Discontinued
0.7202	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7874	Approved
0.72	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6166	Phase 2
0.72	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8455	Phase 2
0.7158	Intermediate Similarity	NPD7698	Approved
0.7158	Intermediate Similarity	NPD7697	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7151	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD3817	Phase 2
0.7135	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD8513	Phase 3
0.7133	Intermediate Similarity	NPD8516	Approved
0.7133	Intermediate Similarity	NPD8515	Approved
0.7133	Intermediate Similarity	NPD8517	Approved
0.7119	Intermediate Similarity	NPD3751	Discontinued
0.7118	Intermediate Similarity	NPD6801	Discontinued
0.7101	Intermediate Similarity	NPD4380	Phase 2
0.7098	Intermediate Similarity	NPD7701	Phase 2
0.7093	Intermediate Similarity	NPD7058	Phase 2
0.7093	Intermediate Similarity	NPD7057	Phase 3
0.709	Intermediate Similarity	NPD6780	Approved
0.709	Intermediate Similarity	NPD6779	Approved
0.709	Intermediate Similarity	NPD6782	Approved
0.709	Intermediate Similarity	NPD6781	Approved
0.709	Intermediate Similarity	NPD6776	Approved
0.709	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD6777	Approved
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.707	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7048	Intermediate Similarity	NPD6799	Approved
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7024	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5403	Approved
0.7006	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD6599	Discontinued
0.6994	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3882	Suspended
0.699	Remote Similarity	NPD7801	Approved
0.6977	Remote Similarity	NPD7819	Suspended
0.6973	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5494	Approved
0.6954	Remote Similarity	NPD8462	Phase 1
0.6941	Remote Similarity	NPD7458	Discontinued
0.6919	Remote Similarity	NPD37	Approved
0.6897	Remote Similarity	NPD4967	Phase 2
0.6897	Remote Similarity	NPD4965	Approved
0.6897	Remote Similarity	NPD4966	Approved
0.6867	Remote Similarity	NPD4628	Phase 3
0.6863	Remote Similarity	NPD5126	Approved
0.6863	Remote Similarity	NPD5125	Phase 3
0.6854	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1934	Approved
0.6818	Remote Similarity	NPD8328	Phase 3
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD6234	Discontinued
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8404	Phase 2
0.68	Remote Similarity	NPD2629	Approved
0.6782	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7473	Discontinued
0.6772	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6212	Phase 3
0.6772	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6213	Phase 3
0.677	Remote Similarity	NPD7961	Discontinued
0.6763	Remote Similarity	NPD7411	Suspended
0.6755	Remote Similarity	NPD4198	Discontinued
0.6753	Remote Similarity	NPD6823	Phase 2
0.6743	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7199	Phase 2
0.6735	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD969	Suspended
0.6703	Remote Similarity	NPD5844	Phase 1
0.6689	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6232	Discontinued
0.6608	Remote Similarity	NPD2532	Approved
0.6608	Remote Similarity	NPD2533	Approved
0.6608	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2534	Approved
0.6606	Remote Similarity	NPD7097	Phase 1
0.6605	Remote Similarity	NPD3764	Approved
0.6595	Remote Similarity	NPD6765	Approved
0.6595	Remote Similarity	NPD6764	Approved
0.6591	Remote Similarity	NPD2801	Approved
0.6585	Remote Similarity	NPD6355	Discontinued
0.6577	Remote Similarity	NPD2067	Discontinued
0.6573	Remote Similarity	NPD3749	Approved
0.6568	Remote Similarity	NPD8166	Discontinued
0.6556	Remote Similarity	NPD6959	Discontinued
0.6556	Remote Similarity	NPD8127	Discontinued
0.6548	Remote Similarity	NPD7680	Approved
0.6548	Remote Similarity	NPD1549	Phase 2
0.6536	Remote Similarity	NPD919	Approved
0.6533	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2796	Approved
0.6513	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5760	Phase 2
0.6497	Remote Similarity	NPD5761	Phase 2
0.6497	Remote Similarity	NPD1465	Phase 2
0.6495	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2346	Discontinued
0.6488	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7999	Approved
0.6474	Remote Similarity	NPD1512	Approved
0.6471	Remote Similarity	NPD7930	Approved
0.6471	Remote Similarity	NPD2575	Approved
0.6467	Remote Similarity	NPD1510	Phase 2
0.6467	Remote Similarity	NPD7033	Discontinued
0.6457	Remote Similarity	NPD3226	Approved
0.6457	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6785	Approved
0.6455	Remote Similarity	NPD6784	Approved
0.645	Remote Similarity	NPD7584	Approved
0.6438	Remote Similarity	NPD7736	Approved
0.6429	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7768	Phase 2
0.6419	Remote Similarity	NPD5048	Discontinued
0.641	Remote Similarity	NPD9545	Approved
0.6402	Remote Similarity	NPD2313	Discontinued
0.6402	Remote Similarity	NPD6798	Discontinued
0.64	Remote Similarity	NPD1653	Approved
0.64	Remote Similarity	NPD2182	Approved
0.6398	Remote Similarity	NPD7319	Approved
0.6393	Remote Similarity	NPD3926	Phase 2
0.6386	Remote Similarity	NPD1933	Approved
0.6382	Remote Similarity	NPD7497	Discontinued
0.6375	Remote Similarity	NPD8074	Phase 3
0.6374	Remote Similarity	NPD1247	Approved
0.6369	Remote Similarity	NPD2799	Discontinued
0.6368	Remote Similarity	NPD7583	Approved
0.6368	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8059	Phase 3
0.6364	Remote Similarity	NPD6233	Phase 2
0.6359	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2798	Approved
0.6358	Remote Similarity	NPD1511	Approved
0.6353	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD1237	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data