NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1138.52
Volume:	1086.714
LogP:	2.267
LogD:	2.063
LogS:	-3.463
# Rotatable Bonds:	18
TPSA:	336.34
# H-Bond Aceptor:	24
# H-Bond Donor:	8
# Rings:	10
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.061
Synthetic Accessibility Score:	7.661
Fsp3:	0.839
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:	-6.408
MDCK Permeability:	0.0003985724470112473
Pgp-inhibitor:	0.021
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	41.264949798583984%
Volume Distribution (VD):	0.333
Pgp-substrate:	14.961977005004883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.129
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	0.846
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.721
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.509
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.286
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC477488

Natural Product ID:	NPC477488
*Common Name:**	[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-8-acetyloxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-9-yl] benzoate
IUPAC Name:	[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-8-acetyloxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-9-yl] benzoate
Synonyms:
Standard InCHIKey:	LKCFUIHQVNZJMI-ZDMWUKOVSA-N
Standard InCHI:	InChI=1S/C56H82O24/c1-24(59)31-16-19-56-54(31,6)48(72-27(4)60)46(76-49(67)28-12-10-9-11-13-28)47-53(5)17-15-30(20-29(53)14-18-55(47,56)80-56)73-35-21-32(68-7)42(25(2)70-35)77-52-41(66)45(69-8)43(26(3)71-52)78-51-40(65)38(63)44(34(23-58)75-51)79-50-39(64)37(62)36(61)33(22-57)74-50/h9-13,25-26,29-48,50-52,57-58,61-66H,14-23H2,1-8H3/t25-,26-,29+,30+,31-,32-,33-,34-,35+,36-,37+,38-,39-,40-,41-,42-,43-,44-,45+,46+,47-,48-,50+,51+,52+,53+,54+,55+,56-/m1/s1
SMILES:	C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@H](C2)CC[C@]45[C@@H]3[C@@H]([C@H]([C@]6([C@]4(O5)CC[C@@H]6C(=O)C)C)OC(=O)C)OC(=O)C7=CC=CC=C7)C)OC)O[C@H]8[C@@H]([C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118724165
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO23320	Marsdenia tenacissima	Species	Apocynaceae	Eukaryota	stems	Simao County, Yunnan Province, China	2005-MAR	PMID[25215856]
NPO23320	Marsdenia tenacissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23320	Marsdenia tenacissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Ratio IC50	=	168	n.a.	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	160	nM	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	26800	nM	PMID[25215856]

☑ 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 NPC477488 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	393
0.1-0.2	1389
0.2-0.3	2859
0.3-0.4	5818
0.4-0.5	10151
0.5-0.6	13468
0.6-0.7	6887
0.7-0.8	1369
0.8-0.85	277
0.85-0.9	61
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC477491
0.9434	High Similarity	NPC473557
0.9434	High Similarity	NPC473468
0.9434	High Similarity	NPC475567
0.9375	High Similarity	NPC475175
0.9375	High Similarity	NPC475198
0.9375	High Similarity	NPC475531
0.9299	High Similarity	NPC476784
0.9125	High Similarity	NPC475536
0.9125	High Similarity	NPC165234
0.9068	High Similarity	NPC473641
0.9068	High Similarity	NPC475437
0.9068	High Similarity	NPC475505
0.9068	High Similarity	NPC475300
0.9068	High Similarity	NPC473797
0.9068	High Similarity	NPC475464
0.8951	High Similarity	NPC478125
0.8909	High Similarity	NPC477471
0.8909	High Similarity	NPC477466
0.8909	High Similarity	NPC477473
0.8909	High Similarity	NPC477469
0.8889	High Similarity	NPC478124
0.8868	High Similarity	NPC469456
0.8848	High Similarity	NPC40138
0.882	High Similarity	NPC319404
0.8805	High Similarity	NPC472657
0.8805	High Similarity	NPC472658
0.8765	High Similarity	NPC477623
0.8765	High Similarity	NPC471138
0.8765	High Similarity	NPC309991
0.8765	High Similarity	NPC323356
0.8765	High Similarity	NPC475613
0.8765	High Similarity	NPC326328
0.875	High Similarity	NPC469421
0.8735	High Similarity	NPC102465
0.8735	High Similarity	NPC469420
0.8734	High Similarity	NPC476173
0.872	High Similarity	NPC329960
0.872	High Similarity	NPC150893
0.872	High Similarity	NPC295408
0.8704	High Similarity	NPC469399
0.8704	High Similarity	NPC477736
0.8696	High Similarity	NPC475548
0.8696	High Similarity	NPC475638
0.8696	High Similarity	NPC290683
0.8679	High Similarity	NPC478123
0.8671	High Similarity	NPC474564
0.8642	High Similarity	NPC469417
0.8642	High Similarity	NPC322048
0.8642	High Similarity	NPC477735
0.8642	High Similarity	NPC318447
0.8634	High Similarity	NPC469398
0.8625	High Similarity	NPC477905
0.8616	High Similarity	NPC476092
0.8616	High Similarity	NPC475218
0.8616	High Similarity	NPC475447
0.8616	High Similarity	NPC70236
0.8614	High Similarity	NPC61891
0.8614	High Similarity	NPC325732
0.8614	High Similarity	NPC324769
0.858	High Similarity	NPC323001
0.858	High Similarity	NPC326235
0.8571	High Similarity	NPC471135
0.8571	High Similarity	NPC469477
0.8571	High Similarity	NPC133430
0.8545	High Similarity	NPC477188
0.8545	High Similarity	NPC477190
0.8545	High Similarity	NPC43304
0.8523	High Similarity	NPC189704
0.8519	High Similarity	NPC132599
0.8519	High Similarity	NPC469422
0.8519	High Similarity	NPC34066
0.8519	High Similarity	NPC471176
0.8519	High Similarity	NPC5115
0.8519	High Similarity	NPC473611
0.8519	High Similarity	NPC228204
0.8519	High Similarity	NPC469730
0.8519	High Similarity	NPC26033
0.8519	High Similarity	NPC473632
0.8509	High Similarity	NPC472548
0.85	High Similarity	NPC7095
0.85	High Similarity	NPC469448
0.8494	Intermediate Similarity	NPC478073
0.8494	Intermediate Similarity	NPC66193
0.8485	Intermediate Similarity	NPC476077
0.8481	Intermediate Similarity	NPC171525
0.8481	Intermediate Similarity	NPC177940
0.8481	Intermediate Similarity	NPC470159
0.8481	Intermediate Similarity	NPC473088
0.8481	Intermediate Similarity	NPC469349
0.8481	Intermediate Similarity	NPC472575
0.8481	Intermediate Similarity	NPC29704
0.8481	Intermediate Similarity	NPC472571
0.8481	Intermediate Similarity	NPC184817
0.8481	Intermediate Similarity	NPC200471
0.8481	Intermediate Similarity	NPC174982
0.8481	Intermediate Similarity	NPC96903
0.8481	Intermediate Similarity	NPC472568
0.8481	Intermediate Similarity	NPC472572
0.8481	Intermediate Similarity	NPC470157
0.8481	Intermediate Similarity	NPC158663
0.8481	Intermediate Similarity	NPC476973
0.8481	Intermediate Similarity	NPC70403
0.8481	Intermediate Similarity	NPC471104
0.8476	Intermediate Similarity	NPC477467
0.8475	Intermediate Similarity	NPC476067
0.8475	Intermediate Similarity	NPC475121
0.8471	Intermediate Similarity	NPC477894
0.8466	Intermediate Similarity	NPC106895
0.8466	Intermediate Similarity	NPC96194
0.8466	Intermediate Similarity	NPC299855
0.8457	Intermediate Similarity	NPC265395
0.8457	Intermediate Similarity	NPC257213
0.8457	Intermediate Similarity	NPC472005
0.8457	Intermediate Similarity	NPC237549
0.8457	Intermediate Similarity	NPC472030
0.8457	Intermediate Similarity	NPC256142
0.8457	Intermediate Similarity	NPC242262
0.8457	Intermediate Similarity	NPC473414
0.8457	Intermediate Similarity	NPC304876
0.8457	Intermediate Similarity	NPC473205
0.8457	Intermediate Similarity	NPC472022
0.8457	Intermediate Similarity	NPC249471
0.8457	Intermediate Similarity	NPC1173
0.8457	Intermediate Similarity	NPC158333
0.8457	Intermediate Similarity	NPC473776
0.8447	Intermediate Similarity	NPC62792
0.8447	Intermediate Similarity	NPC298072
0.8447	Intermediate Similarity	NPC469415
0.8443	Intermediate Similarity	NPC471493
0.8443	Intermediate Similarity	NPC471134
0.8438	Intermediate Similarity	NPC81698
0.8438	Intermediate Similarity	NPC301556
0.8438	Intermediate Similarity	NPC266265
0.8438	Intermediate Similarity	NPC471101
0.8438	Intermediate Similarity	NPC270590
0.8438	Intermediate Similarity	NPC92293
0.8438	Intermediate Similarity	NPC250046
0.8438	Intermediate Similarity	NPC60509
0.8434	Intermediate Similarity	NPC275477
0.843	Intermediate Similarity	NPC195972
0.8428	Intermediate Similarity	NPC473602
0.8418	Intermediate Similarity	NPC472569
0.8418	Intermediate Similarity	NPC111466
0.8418	Intermediate Similarity	NPC472573
0.8418	Intermediate Similarity	NPC475122
0.8418	Intermediate Similarity	NPC163719
0.8418	Intermediate Similarity	NPC11685
0.8418	Intermediate Similarity	NPC475759
0.8418	Intermediate Similarity	NPC470152
0.8418	Intermediate Similarity	NPC70716
0.8418	Intermediate Similarity	NPC95265
0.8418	Intermediate Similarity	NPC241951
0.8418	Intermediate Similarity	NPC472570
0.8418	Intermediate Similarity	NPC25768
0.8418	Intermediate Similarity	NPC95810
0.8418	Intermediate Similarity	NPC57628
0.8418	Intermediate Similarity	NPC125106
0.8418	Intermediate Similarity	NPC188865
0.8418	Intermediate Similarity	NPC476974
0.8415	Intermediate Similarity	NPC477474
0.8415	Intermediate Similarity	NPC477472
0.8415	Intermediate Similarity	NPC477470
0.8405	Intermediate Similarity	NPC114410
0.8405	Intermediate Similarity	NPC282239
0.8405	Intermediate Similarity	NPC472549
0.8405	Intermediate Similarity	NPC112523
0.8385	Intermediate Similarity	NPC222102
0.8385	Intermediate Similarity	NPC165260
0.8385	Intermediate Similarity	NPC112216
0.8385	Intermediate Similarity	NPC473214
0.8385	Intermediate Similarity	NPC470245
0.8385	Intermediate Similarity	NPC198455
0.8385	Intermediate Similarity	NPC161239
0.8385	Intermediate Similarity	NPC303429
0.8383	Intermediate Similarity	NPC322420
0.838	Intermediate Similarity	NPC112708
0.8375	Intermediate Similarity	NPC281717
0.8372	Intermediate Similarity	NPC477617
0.8365	Intermediate Similarity	NPC40085
0.8365	Intermediate Similarity	NPC264270
0.8365	Intermediate Similarity	NPC472556
0.8364	Intermediate Similarity	NPC471102
0.8364	Intermediate Similarity	NPC49297
0.8354	Intermediate Similarity	NPC163087
0.8354	Intermediate Similarity	NPC70344
0.8354	Intermediate Similarity	NPC154675
0.8354	Intermediate Similarity	NPC91703
0.8344	Intermediate Similarity	NPC118080
0.8344	Intermediate Similarity	NPC291599
0.8344	Intermediate Similarity	NPC27377
0.8344	Intermediate Similarity	NPC87448
0.8344	Intermediate Similarity	NPC41481
0.8344	Intermediate Similarity	NPC97947
0.8344	Intermediate Similarity	NPC77719
0.8344	Intermediate Similarity	NPC472576
0.8344	Intermediate Similarity	NPC16912
0.8333	Intermediate Similarity	NPC471103
0.8333	Intermediate Similarity	NPC473711
0.8333	Intermediate Similarity	NPC475299

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 NPC477488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	848
0.2-0.3	1925
0.3-0.4	3160
0.4-0.5	1985
0.5-0.6	731
0.6-0.7	149
0.7-0.8	23
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
0.8304	Intermediate Similarity	NPD7799	Discontinued
0.8025	Intermediate Similarity	NPD7236	Approved
0.7892	Intermediate Similarity	NPD7239	Suspended
0.774	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8368	Discontinued
0.7709	Intermediate Similarity	NPD7685	Pre-registration
0.768	Intermediate Similarity	NPD8407	Phase 2
0.7541	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7058	Phase 2
0.7471	Intermediate Similarity	NPD7057	Phase 3
0.7432	Intermediate Similarity	NPD8313	Approved
0.7432	Intermediate Similarity	NPD8312	Approved
0.7419	Intermediate Similarity	NPD8361	Approved
0.7419	Intermediate Similarity	NPD8360	Approved
0.7419	Intermediate Similarity	NPD8435	Approved
0.7405	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8434	Phase 2
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7282	Intermediate Similarity	NPD8319	Approved
0.724	Intermediate Similarity	NPD7700	Phase 2
0.724	Intermediate Similarity	NPD7699	Phase 2
0.7188	Intermediate Similarity	NPD8485	Approved
0.716	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD7497	Discontinued
0.7134	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8150	Discontinued
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7111	Intermediate Similarity	NPD8127	Discontinued
0.7104	Intermediate Similarity	NPD7228	Approved
0.7083	Intermediate Similarity	NPD6534	Approved
0.7083	Intermediate Similarity	NPD6535	Approved
0.7073	Intermediate Similarity	NPD7961	Discontinued
0.7056	Intermediate Similarity	NPD7435	Discontinued
0.7043	Intermediate Similarity	NPD7240	Approved
0.7027	Intermediate Similarity	NPD7074	Phase 3
0.6973	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7698	Approved
0.697	Remote Similarity	NPD7697	Approved
0.697	Remote Similarity	NPD7696	Phase 3
0.6965	Remote Similarity	NPD8151	Discontinued
0.6963	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6273	Approved
0.6937	Remote Similarity	NPD7507	Approved
0.6935	Remote Similarity	NPD7472	Approved
0.6931	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7874	Approved
0.6915	Remote Similarity	NPD7701	Phase 2
0.6915	Remote Similarity	NPD7808	Phase 3
0.6914	Remote Similarity	NPD7319	Approved
0.6904	Remote Similarity	NPD6781	Approved
0.6904	Remote Similarity	NPD6776	Approved
0.6904	Remote Similarity	NPD6778	Approved
0.6904	Remote Similarity	NPD6782	Approved
0.6904	Remote Similarity	NPD6780	Approved
0.6904	Remote Similarity	NPD6777	Approved
0.6904	Remote Similarity	NPD6779	Approved
0.6899	Remote Similarity	NPD8379	Approved
0.6899	Remote Similarity	NPD8335	Approved
0.6899	Remote Similarity	NPD8296	Approved
0.6899	Remote Similarity	NPD8380	Approved
0.6899	Remote Similarity	NPD8378	Approved
0.6898	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3787	Discontinued
0.6882	Remote Similarity	NPD7054	Approved
0.6872	Remote Similarity	NPD5761	Phase 2
0.6872	Remote Similarity	NPD5760	Phase 2
0.6871	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7251	Discontinued
0.686	Remote Similarity	NPD8166	Discontinued
0.6851	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7870	Phase 2
0.685	Remote Similarity	NPD7871	Phase 2
0.6835	Remote Similarity	NPD7741	Discontinued
0.6835	Remote Similarity	NPD8294	Approved
0.6835	Remote Similarity	NPD8377	Approved
0.6831	Remote Similarity	NPD7199	Phase 2
0.6828	Remote Similarity	NPD3751	Discontinued
0.6816	Remote Similarity	NPD37	Approved
0.6814	Remote Similarity	NPD7801	Approved
0.6814	Remote Similarity	NPD7783	Phase 2
0.6814	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6797	Phase 2
0.6796	Remote Similarity	NPD4967	Phase 2
0.6796	Remote Similarity	NPD4965	Approved
0.6796	Remote Similarity	NPD4966	Approved
0.6792	Remote Similarity	NPD8033	Approved
0.6791	Remote Similarity	NPD5844	Phase 1
0.6784	Remote Similarity	NPD7266	Discontinued
0.6772	Remote Similarity	NPD7516	Approved
0.6772	Remote Similarity	NPD6765	Approved
0.6772	Remote Similarity	NPD6764	Approved
0.6769	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6212	Phase 3
0.6769	Remote Similarity	NPD6213	Phase 3
0.6763	Remote Similarity	NPD4628	Phase 3
0.675	Remote Similarity	NPD6823	Phase 2
0.6738	Remote Similarity	NPD3818	Discontinued
0.6737	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6190	Approved
0.6721	Remote Similarity	NPD6234	Discontinued
0.6709	Remote Similarity	NPD7327	Approved
0.6709	Remote Similarity	NPD7328	Approved
0.6708	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7028	Phase 2
0.6703	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8462	Phase 1
0.6687	Remote Similarity	NPD7503	Approved
0.6685	Remote Similarity	NPD7819	Suspended
0.6684	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8133	Approved
0.6647	Remote Similarity	NPD7008	Discontinued
0.6646	Remote Similarity	NPD5125	Phase 3
0.6646	Remote Similarity	NPD5126	Approved
0.6632	Remote Similarity	NPD6785	Approved
0.6632	Remote Similarity	NPD6784	Approved
0.6629	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4380	Phase 2
0.661	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8328	Phase 3
0.6604	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7473	Discontinued
0.6595	Remote Similarity	NPD5494	Approved
0.6593	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD8516	Approved
0.6584	Remote Similarity	NPD8515	Approved
0.6584	Remote Similarity	NPD8517	Approved
0.6576	Remote Similarity	NPD7075	Discontinued
0.6571	Remote Similarity	NPD8404	Phase 2
0.6569	Remote Similarity	NPD7999	Approved
0.6562	Remote Similarity	NPD7610	Discontinued
0.6561	Remote Similarity	NPD7094	Approved
0.6561	Remote Similarity	NPD6858	Approved
0.6545	Remote Similarity	NPD7736	Approved
0.6543	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6166	Phase 2
0.6512	Remote Similarity	NPD7097	Phase 1
0.6494	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8513	Phase 3
0.6478	Remote Similarity	NPD2629	Approved
0.6476	Remote Similarity	NPD7930	Approved
0.6471	Remote Similarity	NPD6959	Discontinued
0.6471	Remote Similarity	NPD6663	Approved
0.6471	Remote Similarity	NPD7680	Approved
0.6467	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4198	Discontinued
0.6436	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6232	Discontinued
0.6429	Remote Similarity	NPD6599	Discontinued
0.6429	Remote Similarity	NPD5736	Approved
0.6412	Remote Similarity	NPD3764	Approved
0.64	Remote Similarity	NPD5763	Approved
0.64	Remote Similarity	NPD5762	Approved
0.6393	Remote Similarity	NPD7411	Suspended
0.6384	Remote Similarity	NPD7003	Approved
0.6379	Remote Similarity	NPD7305	Phase 1
0.6378	Remote Similarity	NPD5402	Approved
0.6376	Remote Similarity	NPD8059	Phase 3
0.6376	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6801	Discontinued
0.6335	Remote Similarity	NPD7115	Discovery
0.6329	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6674	Discontinued
0.6324	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD1465	Phase 2
0.6301	Remote Similarity	NPD230	Phase 1
0.6292	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3817	Phase 2
0.6284	Remote Similarity	NPD3226	Approved
0.6284	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD8285	Discontinued
0.6273	Remote Similarity	NPD5951	Approved
0.6272	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6085	Phase 2
0.627	Remote Similarity	NPD1934	Approved
0.6257	Remote Similarity	NPD7768	Phase 2
0.6257	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD2534	Approved
0.6243	Remote Similarity	NPD2532	Approved
0.6243	Remote Similarity	NPD4140	Approved
0.6243	Remote Similarity	NPD2533	Approved
0.6242	Remote Similarity	NPD6686	Approved
0.6242	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD3749	Approved
0.622	Remote Similarity	NPD7009	Phase 2
0.6215	Remote Similarity	NPD6005	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