NPASS Compound

Structure

NPC29607 OpenBabel07101718242D 31 32 0 0 1 0 0 0 0 0999 V2000 -3.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 0.8660 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 13 1 0 0 0 0 9 29 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 30 1 0 0 0 0 14 12 1 1 0 0 0 14 17 1 0 0 0 0 14 31 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 29 1 1 0 0 0 20 31 1 0 0 0 0 21 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.17
Volume:	426.743
LogP:	0.098
LogD:	-0.857
LogS:	-1.334
# Rotatable Bonds:	11
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	4.066
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.007
MDCK Permeability:	1.3597291399491951e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.783
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.758

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	58.38751220703125%
Volume Distribution (VD):	0.381
Pgp-substrate:	25.069358825683594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.415
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.539
Carcinogencity:	0.089
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC29607

Natural Product ID:	NPC29607
*Common Name:**	Longumoside B
IUPAC Name:	3-methyl-3-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(E)-3-phenylprop-2-enoxy]oxan-2-yl]methoxy]pentanedioic acid
Synonyms:	Longumoside B
Standard InCHIKey:	XCAAQXCIKODIDY-QUNBHGSGSA-N
Standard InCHI:	InChI=1S/C21H28O10/c1-21(10-15(22)23,11-16(24)25)30-12-14-17(26)18(27)19(28)20(31-14)29-9-5-8-13-6-3-2-4-7-13/h2-8,14,17-20,26-28H,9-12H2,1H3,(H,22,23)(H,24,25)/b8-5+/t14-,17-,18+,19-,20-/m1/s1
SMILES:	OC(=O)CC(CC(=O)O)(OC[C@H]1O[C@@H](OC/C=C/c2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2347639
PubChem CID:	71579641
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
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872768]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20839888]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434420]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26237	Piper longum	Species	Piperaceae	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	2
Others	1

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	3750000.0	nM	PMID[508129]
NPT27	Others	Unspecified		CC50	>	3750000.0	nM	PMID[508129]

☑ 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 NPC29607 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	202
0.1-0.2	862
0.2-0.3	2542
0.3-0.4	7378
0.4-0.5	12133
0.5-0.6	15590
0.6-0.7	3626
0.7-0.8	338
0.8-0.85	21
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8899	High Similarity	NPC184633
0.8829	High Similarity	NPC470825
0.8739	High Similarity	NPC43584
0.8673	High Similarity	NPC474641
0.8611	High Similarity	NPC469527
0.8417	Intermediate Similarity	NPC140561
0.8417	Intermediate Similarity	NPC141970
0.8387	Intermediate Similarity	NPC469549
0.8347	Intermediate Similarity	NPC138798
0.8346	Intermediate Similarity	NPC471029
0.8279	Intermediate Similarity	NPC57607
0.8279	Intermediate Similarity	NPC162925
0.8279	Intermediate Similarity	NPC87153
0.8279	Intermediate Similarity	NPC244454
0.8246	Intermediate Similarity	NPC30563
0.8246	Intermediate Similarity	NPC264784
0.8226	Intermediate Similarity	NPC231627
0.8211	Intermediate Similarity	NPC28069
0.8211	Intermediate Similarity	NPC77651
0.816	Intermediate Similarity	NPC226101
0.816	Intermediate Similarity	NPC237182
0.8158	Intermediate Similarity	NPC276061
0.8158	Intermediate Similarity	NPC474148
0.8145	Intermediate Similarity	NPC290276
0.8145	Intermediate Similarity	NPC10121
0.8145	Intermediate Similarity	NPC35338
0.8145	Intermediate Similarity	NPC198918
0.8145	Intermediate Similarity	NPC204214
0.8145	Intermediate Similarity	NPC63404
0.8145	Intermediate Similarity	NPC10883
0.8145	Intermediate Similarity	NPC231888
0.8145	Intermediate Similarity	NPC124878
0.8145	Intermediate Similarity	NPC92283
0.813	Intermediate Similarity	NPC317163
0.8125	Intermediate Similarity	NPC37714
0.8125	Intermediate Similarity	NPC152384
0.811	Intermediate Similarity	NPC281798
0.8099	Intermediate Similarity	NPC229600
0.808	Intermediate Similarity	NPC471025
0.8036	Intermediate Similarity	NPC47286
0.8016	Intermediate Similarity	NPC471024
0.8	Intermediate Similarity	NPC114096
0.7984	Intermediate Similarity	NPC470143
0.7984	Intermediate Similarity	NPC322503
0.7984	Intermediate Similarity	NPC145287
0.7953	Intermediate Similarity	NPC11025
0.7939	Intermediate Similarity	NPC472132
0.7937	Intermediate Similarity	NPC148026
0.7934	Intermediate Similarity	NPC476096
0.7923	Intermediate Similarity	NPC169398
0.7909	Intermediate Similarity	NPC262826
0.7891	Intermediate Similarity	NPC319995
0.7891	Intermediate Similarity	NPC17567
0.7891	Intermediate Similarity	NPC289415
0.7874	Intermediate Similarity	NPC301857
0.7857	Intermediate Similarity	NPC267733
0.7857	Intermediate Similarity	NPC276047
0.7857	Intermediate Similarity	NPC147032
0.7823	Intermediate Similarity	NPC52097
0.7795	Intermediate Similarity	NPC106677
0.7786	Intermediate Similarity	NPC34456
0.7778	Intermediate Similarity	NPC123704
0.776	Intermediate Similarity	NPC473881
0.7744	Intermediate Similarity	NPC469364
0.7744	Intermediate Similarity	NPC65262
0.7744	Intermediate Similarity	NPC101686
0.7742	Intermediate Similarity	NPC11724
0.7731	Intermediate Similarity	NPC172525
0.7719	Intermediate Similarity	NPC148060
0.7717	Intermediate Similarity	NPC471026
0.7717	Intermediate Similarity	NPC252114
0.7717	Intermediate Similarity	NPC471157
0.7687	Intermediate Similarity	NPC220942
0.7672	Intermediate Similarity	NPC20485
0.7664	Intermediate Similarity	NPC63304
0.7661	Intermediate Similarity	NPC476872
0.7656	Intermediate Similarity	NPC156692
0.7656	Intermediate Similarity	NPC173150
0.7656	Intermediate Similarity	NPC471881
0.7656	Intermediate Similarity	NPC175333
0.7656	Intermediate Similarity	NPC45224
0.7656	Intermediate Similarity	NPC471882
0.7656	Intermediate Similarity	NPC35288
0.7638	Intermediate Similarity	NPC126991
0.7638	Intermediate Similarity	NPC83218
0.7634	Intermediate Similarity	NPC269421
0.7623	Intermediate Similarity	NPC266389
0.7623	Intermediate Similarity	NPC122245
0.7623	Intermediate Similarity	NPC216605
0.7583	Intermediate Similarity	NPC120217
0.7576	Intermediate Similarity	NPC114116
0.7568	Intermediate Similarity	NPC30361
0.7556	Intermediate Similarity	NPC220936
0.7556	Intermediate Similarity	NPC31745
0.7554	Intermediate Similarity	NPC143246
0.7554	Intermediate Similarity	NPC119773
0.7554	Intermediate Similarity	NPC475539
0.7554	Intermediate Similarity	NPC212808
0.7554	Intermediate Similarity	NPC474268
0.7538	Intermediate Similarity	NPC295970
0.7537	Intermediate Similarity	NPC470572
0.7521	Intermediate Similarity	NPC313193
0.7519	Intermediate Similarity	NPC288416
0.7518	Intermediate Similarity	NPC284957
0.7518	Intermediate Similarity	NPC296643
0.75	Intermediate Similarity	NPC476033
0.75	Intermediate Similarity	NPC79608
0.7482	Intermediate Similarity	NPC475528
0.7481	Intermediate Similarity	NPC305162
0.7481	Intermediate Similarity	NPC469705
0.7481	Intermediate Similarity	NPC17968
0.7481	Intermediate Similarity	NPC470122
0.7481	Intermediate Similarity	NPC475195
0.7464	Intermediate Similarity	NPC469367
0.7462	Intermediate Similarity	NPC225307
0.7462	Intermediate Similarity	NPC158673
0.7444	Intermediate Similarity	NPC136608
0.7444	Intermediate Similarity	NPC38420
0.7444	Intermediate Similarity	NPC164172
0.7444	Intermediate Similarity	NPC254398
0.7442	Intermediate Similarity	NPC61181
0.7426	Intermediate Similarity	NPC62800
0.7426	Intermediate Similarity	NPC324262
0.7424	Intermediate Similarity	NPC246869
0.7424	Intermediate Similarity	NPC138777
0.7424	Intermediate Similarity	NPC46137
0.7424	Intermediate Similarity	NPC478255
0.7424	Intermediate Similarity	NPC235294
0.7424	Intermediate Similarity	NPC225384
0.7414	Intermediate Similarity	NPC19136
0.7407	Intermediate Similarity	NPC471345
0.7405	Intermediate Similarity	NPC253595
0.7405	Intermediate Similarity	NPC27712
0.7405	Intermediate Similarity	NPC477294
0.7405	Intermediate Similarity	NPC477293
0.7405	Intermediate Similarity	NPC229784
0.7398	Intermediate Similarity	NPC175771
0.7398	Intermediate Similarity	NPC148055
0.7385	Intermediate Similarity	NPC103533
0.7381	Intermediate Similarity	NPC476448
0.7381	Intermediate Similarity	NPC469548
0.7381	Intermediate Similarity	NPC476445
0.7372	Intermediate Similarity	NPC77493
0.7368	Intermediate Similarity	NPC471095
0.7368	Intermediate Similarity	NPC473924
0.7368	Intermediate Similarity	NPC471066
0.7368	Intermediate Similarity	NPC473285
0.7364	Intermediate Similarity	NPC470816
0.7357	Intermediate Similarity	NPC477737
0.7338	Intermediate Similarity	NPC475213
0.7338	Intermediate Similarity	NPC152796
0.7338	Intermediate Similarity	NPC478250
0.7338	Intermediate Similarity	NPC242756
0.7338	Intermediate Similarity	NPC293154
0.7328	Intermediate Similarity	NPC146540
0.7328	Intermediate Similarity	NPC198487
0.7328	Intermediate Similarity	NPC232880
0.7319	Intermediate Similarity	NPC80098
0.7317	Intermediate Similarity	NPC210531
0.7313	Intermediate Similarity	NPC215484
0.7302	Intermediate Similarity	NPC469702
0.7302	Intermediate Similarity	NPC282409
0.7295	Intermediate Similarity	NPC87069
0.7295	Intermediate Similarity	NPC474363
0.7293	Intermediate Similarity	NPC219677
0.7293	Intermediate Similarity	NPC476407
0.7293	Intermediate Similarity	NPC254819
0.7292	Intermediate Similarity	NPC474620
0.7292	Intermediate Similarity	NPC469477
0.7292	Intermediate Similarity	NPC133430
0.7288	Intermediate Similarity	NPC474111
0.7288	Intermediate Similarity	NPC474376
0.7288	Intermediate Similarity	NPC475203
0.7288	Intermediate Similarity	NPC472315
0.7288	Intermediate Similarity	NPC136962
0.7288	Intermediate Similarity	NPC472316
0.7288	Intermediate Similarity	NPC329705
0.7287	Intermediate Similarity	NPC287429
0.7286	Intermediate Similarity	NPC296659
0.7286	Intermediate Similarity	NPC202391
0.7281	Intermediate Similarity	NPC271475
0.7273	Intermediate Similarity	NPC329657
0.7266	Intermediate Similarity	NPC469623
0.7266	Intermediate Similarity	NPC476142
0.7266	Intermediate Similarity	NPC148080
0.7259	Intermediate Similarity	NPC471883
0.7254	Intermediate Similarity	NPC474422
0.7252	Intermediate Similarity	NPC476873
0.7244	Intermediate Similarity	NPC469412
0.7244	Intermediate Similarity	NPC198734
0.7239	Intermediate Similarity	NPC159811
0.7236	Intermediate Similarity	NPC157338
0.7231	Intermediate Similarity	NPC470510
0.7226	Intermediate Similarity	NPC469696
0.7226	Intermediate Similarity	NPC310252
0.7226	Intermediate Similarity	NPC100558
0.7226	Intermediate Similarity	NPC84789
0.7226	Intermediate Similarity	NPC302583
0.7222	Intermediate Similarity	NPC14950
0.7214	Intermediate Similarity	NPC111466

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 NPC29607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	624
0.2-0.3	1591
0.3-0.4	3355
0.4-0.5	2317
0.5-0.6	945
0.6-0.7	137
0.7-0.8	8
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
0.8189	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD5048	Discontinued
0.7554	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6010	Discontinued
0.7273	Intermediate Similarity	NPD969	Suspended
0.7165	Intermediate Similarity	NPD5125	Phase 3
0.7165	Intermediate Similarity	NPD5126	Approved
0.7143	Intermediate Similarity	NPD6685	Approved
0.7054	Intermediate Similarity	NPD1091	Approved
0.705	Intermediate Similarity	NPD7266	Discontinued
0.7034	Intermediate Similarity	NPD6647	Phase 2
0.6891	Remote Similarity	NPD5765	Approved
0.6891	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD689	Discontinued
0.6855	Remote Similarity	NPD6912	Phase 3
0.6829	Remote Similarity	NPD2067	Discontinued
0.6825	Remote Similarity	NPD2629	Approved
0.678	Remote Similarity	NPD7798	Approved
0.6772	Remote Similarity	NPD4198	Discontinued
0.6696	Remote Similarity	NPD1282	Approved
0.6695	Remote Similarity	NPD9495	Approved
0.6667	Remote Similarity	NPD2575	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6621	Remote Similarity	NPD6190	Approved
0.6596	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8455	Phase 2
0.6569	Remote Similarity	NPD2613	Approved
0.6558	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5909	Discontinued
0.6496	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7097	Phase 1
0.6462	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8515	Approved
0.6439	Remote Similarity	NPD8513	Phase 3
0.6439	Remote Similarity	NPD8517	Approved
0.6439	Remote Similarity	NPD8516	Approved
0.6438	Remote Similarity	NPD7799	Discontinued
0.6429	Remote Similarity	NPD4745	Approved
0.6429	Remote Similarity	NPD4746	Phase 3
0.6429	Remote Similarity	NPD2573	Approved
0.6429	Remote Similarity	NPD2566	Approved
0.6429	Remote Similarity	NPD6233	Phase 2
0.6429	Remote Similarity	NPD3615	Approved
0.6429	Remote Similarity	NPD3090	Approved
0.6429	Remote Similarity	NPD3087	Approved
0.6429	Remote Similarity	NPD3614	Approved
0.6429	Remote Similarity	NPD3616	Approved
0.6429	Remote Similarity	NPD2571	Approved
0.6429	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2570	Approved
0.6429	Remote Similarity	NPD3089	Approved
0.6429	Remote Similarity	NPD2574	Discontinued
0.6429	Remote Similarity	NPD3088	Approved
0.6423	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5647	Approved
0.6417	Remote Similarity	NPD5926	Approved
0.6417	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5305	Approved
0.6391	Remote Similarity	NPD5306	Approved
0.6379	Remote Similarity	NPD3673	Approved
0.6379	Remote Similarity	NPD3672	Approved
0.637	Remote Similarity	NPD6637	Approved
0.6364	Remote Similarity	NPD9545	Approved
0.6358	Remote Similarity	NPD1653	Approved
0.6357	Remote Similarity	NPD2652	Approved
0.6357	Remote Similarity	NPD2650	Approved
0.6357	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.635	Remote Similarity	NPD2625	Approved
0.635	Remote Similarity	NPD2627	Approved
0.635	Remote Similarity	NPD2626	Approved
0.635	Remote Similarity	NPD2159	Approved
0.635	Remote Similarity	NPD2628	Approved
0.635	Remote Similarity	NPD2160	Approved
0.6349	Remote Similarity	NPD2182	Approved
0.6343	Remote Similarity	NPD4135	Approved
0.6343	Remote Similarity	NPD4106	Approved
0.6343	Remote Similarity	NPD4136	Approved
0.6338	Remote Similarity	NPD4684	Phase 3
0.6338	Remote Similarity	NPD4686	Approved
0.6338	Remote Similarity	NPD4685	Phase 3
0.6336	Remote Similarity	NPD5291	Approved
0.6336	Remote Similarity	NPD5292	Approved
0.6327	Remote Similarity	NPD4628	Phase 3
0.6325	Remote Similarity	NPD7983	Approved
0.6308	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD226	Approved
0.6296	Remote Similarity	NPD4807	Approved
0.6296	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2610	Approved
0.6296	Remote Similarity	NPD2612	Approved
0.6296	Remote Similarity	NPD4215	Approved
0.6296	Remote Similarity	NPD2608	Approved
0.6296	Remote Similarity	NPD4806	Approved
0.6296	Remote Similarity	NPD3132	Approved
0.6296	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3131	Approved
0.6296	Remote Similarity	NPD4218	Approved
0.6296	Remote Similarity	NPD4216	Approved
0.6296	Remote Similarity	NPD7054	Approved
0.6296	Remote Similarity	NPD2609	Approved
0.6296	Remote Similarity	NPD4217	Approved
0.6296	Remote Similarity	NPD2611	Approved
0.6294	Remote Similarity	NPD6653	Approved
0.6293	Remote Similarity	NPD5347	Phase 2
0.6293	Remote Similarity	NPD5346	Phase 2
0.628	Remote Similarity	NPD7685	Pre-registration
0.627	Remote Similarity	NPD6686	Approved
0.6269	Remote Similarity	NPD1778	Approved
0.6261	Remote Similarity	NPD4793	Discontinued
0.6258	Remote Similarity	NPD7472	Approved
0.6258	Remote Similarity	NPD7074	Phase 3
0.625	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1989	Approved
0.625	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD7741	Discontinued
0.6241	Remote Similarity	NPD6798	Discontinued
0.623	Remote Similarity	NPD1238	Approved
0.622	Remote Similarity	NPD6797	Phase 2
0.6216	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4620	Approved
0.6214	Remote Similarity	NPD4617	Approved
0.6214	Remote Similarity	NPD5203	Approved
0.6214	Remote Similarity	NPD5201	Approved
0.62	Remote Similarity	NPD6799	Approved
0.62	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD4062	Phase 3
0.6195	Remote Similarity	NPD9491	Approved
0.6194	Remote Similarity	NPD8444	Approved
0.6194	Remote Similarity	NPD37	Approved
0.6194	Remote Similarity	NPD4102	Approved
0.6194	Remote Similarity	NPD4105	Approved
0.6188	Remote Similarity	NPD3787	Discontinued
0.6187	Remote Similarity	NPD6085	Phase 2
0.6187	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5403	Approved
0.6182	Remote Similarity	NPD7251	Discontinued
0.6182	Remote Similarity	NPD8368	Discontinued
0.6182	Remote Similarity	NPD6559	Discontinued
0.6178	Remote Similarity	NPD4966	Approved
0.6178	Remote Similarity	NPD4965	Approved
0.6178	Remote Similarity	NPD4967	Phase 2
0.6174	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4380	Phase 2
0.6159	Remote Similarity	NPD3225	Approved
0.6159	Remote Similarity	NPD5667	Approved
0.6159	Remote Similarity	NPD5401	Approved
0.6154	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD800	Approved
0.6149	Remote Similarity	NPD1652	Phase 2
0.6145	Remote Similarity	NPD7808	Phase 3
0.6143	Remote Similarity	NPD5204	Approved
0.6142	Remote Similarity	NPD1358	Approved
0.6142	Remote Similarity	NPD290	Approved
0.614	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7075	Discontinued
0.6135	Remote Similarity	NPD3818	Discontinued
0.6135	Remote Similarity	NPD7228	Approved
0.6133	Remote Similarity	NPD5058	Phase 3
0.6131	Remote Similarity	NPD8451	Approved
0.6125	Remote Similarity	NPD7199	Phase 2
0.6122	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6004	Phase 3
0.6122	Remote Similarity	NPD6005	Phase 3
0.6122	Remote Similarity	NPD6002	Phase 3
0.6122	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6362	Approved
0.6111	Remote Similarity	NPD1933	Approved
0.6111	Remote Similarity	NPD230	Phase 1
0.6111	Remote Similarity	NPD6355	Discontinued
0.6108	Remote Similarity	NPD8312	Approved
0.6108	Remote Similarity	NPD8313	Approved
0.6103	Remote Similarity	NPD7830	Approved
0.6103	Remote Similarity	NPD7829	Approved
0.6102	Remote Similarity	NPD1086	Approved
0.6102	Remote Similarity	NPD6698	Approved
0.6102	Remote Similarity	NPD1090	Approved
0.6102	Remote Similarity	NPD1089	Approved
0.6102	Remote Similarity	NPD46	Approved
0.6101	Remote Similarity	NPD6234	Discontinued
0.6099	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD2066	Phase 3
0.609	Remote Similarity	NPD6801	Discontinued
0.609	Remote Similarity	NPD9493	Approved
0.6087	Remote Similarity	NPD8448	Approved
0.6083	Remote Similarity	NPD1066	Discontinued
0.6071	Remote Similarity	NPD8407	Phase 2
0.6063	Remote Similarity	NPD467	Phase 1
0.6058	Remote Similarity	NPD3603	Phase 3
0.6053	Remote Similarity	NPD3971	Phase 1
0.6042	Remote Similarity	NPD5120	Approved
0.6042	Remote Similarity	NPD5119	Approved
0.6042	Remote Similarity	NPD5121	Approved
0.6036	Remote Similarity	NPD225	Approved
0.6036	Remote Similarity	NPD227	Approved
0.6033	Remote Similarity	NPD1693	Approved
0.6032	Remote Similarity	NPD164	Approved
0.6031	Remote Similarity	NPD7843	Approved
0.6028	Remote Similarity	NPD3662	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