NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	944.51
Volume:	947.025
LogP:	5.423
LogD:	3.859
LogS:	-5.463
# Rotatable Bonds:	15
TPSA:	196.36
# H-Bond Aceptor:	16
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	6.323
Fsp3:	0.804
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166
MDCK Permeability:	0.0002515287196729332
Pgp-inhibitor:	0.315
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	80.85054779052734%
Volume Distribution (VD):	0.898
Pgp-substrate:	9.468343734741211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.652
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.588
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.625
CYP3A4-substrate:	0.858

ADMET: Excretion

Clearance (CL):	2.309
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.974
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.69
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.641
Skin Sensitization:	0.572
Carcinogencity:	0.307
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC476784

Natural Product ID:	NPC476784
*Common Name:**	[(3S,8R,9S,10R,12R,13S,14S,17S)-17-[(1S)-1-acetyloxyethyl]-3-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-yl] benzoate
IUPAC Name:	[(3S,8R,9S,10R,12R,13S,14S,17S)-17-[(1S)-1-acetyloxyethyl]-3-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-yl] benzoate
Synonyms:
Standard InCHIKey:	AVAZXIOSUORKOF-GTRQNRLRSA-N
Standard InCHI:	InChI=1S/C51H76O16/c1-26(60-30(5)52)34-19-21-51(56)35-17-16-32-22-33(18-20-49(32,6)36(35)23-39(50(34,51)7)65-47(55)31-14-12-11-13-15-31)64-40-24-37(57-8)44(28(3)61-40)66-41-25-38(58-9)45(29(4)62-41)67-48-43(54)46(59-10)42(53)27(2)63-48/h11-16,26-29,33-46,48,53-54,56H,17-25H2,1-10H3/t26-,27+,28+,29+,33-,34+,35+,36-,37-,38-,39+,40+,41-,42+,43+,44+,45+,46+,48-,49-,50-,51-/m0/s1
SMILES:	C[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2OC)O[C@@H]3[C@H](O[C@@H](C[C@@H]3OC)O[C@H]4CC[C@@]5([C@H]6C[C@H]([C@@]7([C@H](CC[C@@]7([C@@H]6CC=C5C4)O)[C@H](C)OC(=O)C)C)OC(=O)C8=CC=CC=C8)C)C)C)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799771
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33621	Caralluma tuberculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]

☑ 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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6.25	ug/ml	PMID[19299148]

☑ 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 NPC476784 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	361
0.1-0.2	1226
0.2-0.3	2680
0.3-0.4	5372
0.4-0.5	9661
0.5-0.6	14334
0.6-0.7	7028
0.7-0.8	1619
0.8-0.85	274
0.85-0.9	111
0.9-0.95	24
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9608	High Similarity	NPC473468
0.9608	High Similarity	NPC475567
0.9608	High Similarity	NPC473557
0.9545	High Similarity	NPC475198
0.9545	High Similarity	NPC475531
0.9545	High Similarity	NPC475175
0.9299	High Similarity	NPC477488
0.9231	High Similarity	NPC477491
0.9091	High Similarity	NPC319404
0.9079	High Similarity	NPC472657
0.9079	High Similarity	NPC472658
0.9032	High Similarity	NPC477623
0.9007	High Similarity	NPC476173
0.8981	High Similarity	NPC478125
0.894	High Similarity	NPC474564
0.8917	High Similarity	NPC478124
0.8917	High Similarity	NPC165234
0.8917	High Similarity	NPC475536
0.8903	High Similarity	NPC318447
0.8903	High Similarity	NPC322048
0.8896	High Similarity	NPC469456
0.8896	High Similarity	NPC469398
0.8882	High Similarity	NPC476092
0.8882	High Similarity	NPC475447
0.8882	High Similarity	NPC475218
0.8882	High Similarity	NPC469448
0.8882	High Similarity	NPC70236
0.8861	High Similarity	NPC473641
0.8861	High Similarity	NPC473797
0.8861	High Similarity	NPC475464
0.8861	High Similarity	NPC475300
0.8861	High Similarity	NPC475437
0.8861	High Similarity	NPC475505
0.8839	High Similarity	NPC323001
0.8839	High Similarity	NPC326235
0.8831	High Similarity	NPC471135
0.8808	High Similarity	NPC473602
0.879	High Similarity	NPC471138
0.879	High Similarity	NPC326328
0.879	High Similarity	NPC309991
0.879	High Similarity	NPC323356
0.8774	High Similarity	NPC469422
0.8774	High Similarity	NPC34066
0.8758	High Similarity	NPC475561
0.8758	High Similarity	NPC102465
0.8758	High Similarity	NPC475417
0.8742	High Similarity	NPC150893
0.8742	High Similarity	NPC295408
0.8742	High Similarity	NPC329960
0.8718	High Similarity	NPC475548
0.8718	High Similarity	NPC290683
0.8718	High Similarity	NPC475638
0.8701	High Similarity	NPC478123
0.8701	High Similarity	NPC469415
0.8675	High Similarity	NPC111466
0.8658	High Similarity	NPC472547
0.8645	High Similarity	NPC472548
0.8636	High Similarity	NPC222102
0.8636	High Similarity	NPC303429
0.8618	High Similarity	NPC469349
0.8618	High Similarity	NPC472568
0.8618	High Similarity	NPC472575
0.8618	High Similarity	NPC472556
0.8618	High Similarity	NPC471104
0.8618	High Similarity	NPC158663
0.8618	High Similarity	NPC171525
0.8618	High Similarity	NPC473088
0.8618	High Similarity	NPC40085
0.8618	High Similarity	NPC174982
0.8618	High Similarity	NPC472572
0.8618	High Similarity	NPC184817
0.8618	High Similarity	NPC70403
0.8618	High Similarity	NPC96903
0.8618	High Similarity	NPC29704
0.8618	High Similarity	NPC472571
0.8618	High Similarity	NPC177940
0.8618	High Similarity	NPC470159
0.8618	High Similarity	NPC470157
0.8618	High Similarity	NPC200471
0.8618	High Similarity	NPC476973
0.8618	High Similarity	NPC264270
0.8609	High Similarity	NPC91703
0.8608	High Similarity	NPC469399
0.86	High Similarity	NPC118080
0.86	High Similarity	NPC41481
0.86	High Similarity	NPC291599
0.86	High Similarity	NPC16912
0.86	High Similarity	NPC97947
0.86	High Similarity	NPC27377
0.86	High Similarity	NPC87448
0.86	High Similarity	NPC224491
0.86	High Similarity	NPC472576
0.8589	High Similarity	NPC477471
0.8589	High Similarity	NPC477466
0.8589	High Similarity	NPC477473
0.8589	High Similarity	NPC477469
0.8571	High Similarity	NPC301556
0.8571	High Similarity	NPC471101
0.8571	High Similarity	NPC266265
0.8571	High Similarity	NPC270590
0.8571	High Similarity	NPC92293
0.8563	High Similarity	NPC475613
0.8562	High Similarity	NPC312393
0.8562	High Similarity	NPC478263
0.8562	High Similarity	NPC474935
0.8554	High Similarity	NPC195972
0.8553	High Similarity	NPC95265
0.8553	High Similarity	NPC475122
0.8553	High Similarity	NPC472569
0.8553	High Similarity	NPC70716
0.8553	High Similarity	NPC163719
0.8553	High Similarity	NPC241951
0.8553	High Similarity	NPC470152
0.8553	High Similarity	NPC25768
0.8553	High Similarity	NPC57628
0.8553	High Similarity	NPC125106
0.8553	High Similarity	NPC476974
0.8553	High Similarity	NPC188865
0.8553	High Similarity	NPC472570
0.8553	High Similarity	NPC472573
0.8553	High Similarity	NPC475759
0.8553	High Similarity	NPC11685
0.8553	High Similarity	NPC95810
0.8544	High Similarity	NPC469417
0.8544	High Similarity	NPC477735
0.8543	High Similarity	NPC192658
0.8543	High Similarity	NPC475513
0.8543	High Similarity	NPC473755
0.8543	High Similarity	NPC34012
0.8535	High Similarity	NPC5115
0.8535	High Similarity	NPC472549
0.8533	High Similarity	NPC171207
0.8533	High Similarity	NPC97667
0.8533	High Similarity	NPC100913
0.8533	High Similarity	NPC275592
0.8533	High Similarity	NPC90614
0.8528	High Similarity	NPC469420
0.8526	High Similarity	NPC477905
0.8523	High Similarity	NPC39549
0.8514	High Similarity	NPC473399
0.8514	High Similarity	NPC473216
0.8506	High Similarity	NPC327031
0.8506	High Similarity	NPC281717
0.8497	Intermediate Similarity	NPC478264
0.8491	Intermediate Similarity	NPC477736
0.8487	Intermediate Similarity	NPC163087
0.848	Intermediate Similarity	NPC96194
0.848	Intermediate Similarity	NPC299855
0.8477	Intermediate Similarity	NPC266374
0.8471	Intermediate Similarity	NPC469477
0.8471	Intermediate Similarity	NPC133430
0.8462	Intermediate Similarity	NPC96308
0.8462	Intermediate Similarity	NPC62792
0.8462	Intermediate Similarity	NPC298072
0.8456	Intermediate Similarity	NPC472545
0.8456	Intermediate Similarity	NPC472551
0.8452	Intermediate Similarity	NPC476975
0.8452	Intermediate Similarity	NPC76103
0.8446	Intermediate Similarity	NPC48929
0.8434	Intermediate Similarity	NPC469421
0.8431	Intermediate Similarity	NPC34943
0.843	Intermediate Similarity	NPC189704
0.8421	Intermediate Similarity	NPC472546
0.8418	Intermediate Similarity	NPC473611
0.8418	Intermediate Similarity	NPC469730
0.8418	Intermediate Similarity	NPC473632
0.8418	Intermediate Similarity	NPC471176
0.8418	Intermediate Similarity	NPC132599
0.8415	Intermediate Similarity	NPC40138
0.8411	Intermediate Similarity	NPC87934
0.8411	Intermediate Similarity	NPC162613
0.8397	Intermediate Similarity	NPC473214
0.8397	Intermediate Similarity	NPC470245
0.8395	Intermediate Similarity	NPC269668
0.8387	Intermediate Similarity	NPC473760
0.8383	Intermediate Similarity	NPC477617
0.8383	Intermediate Similarity	NPC13989
0.8382	Intermediate Similarity	NPC475121
0.8382	Intermediate Similarity	NPC476067
0.8378	Intermediate Similarity	NPC472248
0.8367	Intermediate Similarity	NPC72915
0.8363	Intermediate Similarity	NPC473205
0.8363	Intermediate Similarity	NPC473776
0.8344	Intermediate Similarity	NPC9905
0.8344	Intermediate Similarity	NPC470153
0.8344	Intermediate Similarity	NPC473301
0.8344	Intermediate Similarity	NPC471493
0.8333	Intermediate Similarity	NPC472374
0.8333	Intermediate Similarity	NPC472372
0.8333	Intermediate Similarity	NPC473215
0.8333	Intermediate Similarity	NPC230670
0.8333	Intermediate Similarity	NPC71385
0.8323	Intermediate Similarity	NPC20255
0.8323	Intermediate Similarity	NPC240115
0.8323	Intermediate Similarity	NPC48599
0.8323	Intermediate Similarity	NPC209592
0.8322	Intermediate Similarity	NPC203486
0.8322	Intermediate Similarity	NPC28836
0.8312	Intermediate Similarity	NPC38696
0.8312	Intermediate Similarity	NPC471139

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 NPC476784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	803
0.2-0.3	1741
0.3-0.4	3071
0.4-0.5	2151
0.5-0.6	876
0.6-0.7	178
0.7-0.8	32
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD7799	Discontinued
0.8258	Intermediate Similarity	NPD7236	Approved
0.8113	Intermediate Similarity	NPD7239	Suspended
0.8047	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7057	Phase 3
0.7665	Intermediate Similarity	NPD7058	Phase 2
0.76	Intermediate Similarity	NPD8368	Discontinued
0.7582	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8407	Phase 2
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.744	Intermediate Similarity	NPD8455	Phase 2
0.7333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD8379	Approved
0.7315	Intermediate Similarity	NPD8296	Approved
0.7315	Intermediate Similarity	NPD8380	Approved
0.7315	Intermediate Similarity	NPD8335	Approved
0.7315	Intermediate Similarity	NPD8378	Approved
0.7308	Intermediate Similarity	NPD8435	Approved
0.7308	Intermediate Similarity	NPD8360	Approved
0.7308	Intermediate Similarity	NPD8361	Approved
0.7293	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8294	Approved
0.7248	Intermediate Similarity	NPD7741	Discontinued
0.7248	Intermediate Similarity	NPD8377	Approved
0.7229	Intermediate Similarity	NPD6273	Approved
0.7215	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7240	Approved
0.72	Intermediate Similarity	NPD7503	Approved
0.72	Intermediate Similarity	NPD8033	Approved
0.7198	Intermediate Similarity	NPD8434	Phase 2
0.7173	Intermediate Similarity	NPD8320	Phase 1
0.7173	Intermediate Similarity	NPD8319	Approved
0.7152	Intermediate Similarity	NPD7961	Discontinued
0.7143	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7507	Approved
0.7105	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD7319	Approved
0.7075	Intermediate Similarity	NPD8133	Approved
0.7066	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7266	Discontinued
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5125	Phase 3
0.7039	Intermediate Similarity	NPD5126	Approved
0.7037	Intermediate Similarity	NPD7700	Phase 2
0.7037	Intermediate Similarity	NPD7699	Phase 2
0.7031	Intermediate Similarity	NPD7497	Discontinued
0.703	Intermediate Similarity	NPD8166	Discontinued
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD7328	Approved
0.6984	Remote Similarity	NPD8485	Approved
0.6977	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD7028	Phase 2
0.6959	Remote Similarity	NPD6858	Approved
0.6959	Remote Similarity	NPD7094	Approved
0.6954	Remote Similarity	NPD7516	Approved
0.6954	Remote Similarity	NPD4966	Approved
0.6954	Remote Similarity	NPD4965	Approved
0.6954	Remote Similarity	NPD4967	Phase 2
0.6936	Remote Similarity	NPD5760	Phase 2
0.6936	Remote Similarity	NPD5761	Phase 2
0.6928	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD6765	Approved
0.6923	Remote Similarity	NPD6764	Approved
0.6923	Remote Similarity	NPD6559	Discontinued
0.6918	Remote Similarity	NPD7008	Discontinued
0.6914	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7472	Approved
0.6893	Remote Similarity	NPD7199	Phase 2
0.6885	Remote Similarity	NPD7808	Phase 3
0.6878	Remote Similarity	NPD6535	Approved
0.6878	Remote Similarity	NPD6534	Approved
0.6875	Remote Similarity	NPD6234	Discontinued
0.6867	Remote Similarity	NPD2629	Approved
0.6856	Remote Similarity	NPD7435	Discontinued
0.6851	Remote Similarity	NPD7054	Approved
0.6845	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6663	Approved
0.6831	Remote Similarity	NPD7251	Discontinued
0.6821	Remote Similarity	NPD4198	Discontinued
0.6792	Remote Similarity	NPD5736	Approved
0.6776	Remote Similarity	NPD6797	Phase 2
0.6774	Remote Similarity	NPD6784	Approved
0.6774	Remote Similarity	NPD6785	Approved
0.6769	Remote Similarity	NPD7698	Approved
0.6769	Remote Similarity	NPD7696	Phase 3
0.6769	Remote Similarity	NPD7697	Approved
0.6768	Remote Similarity	NPD8151	Discontinued
0.6765	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5844	Phase 1
0.6747	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5762	Approved
0.6747	Remote Similarity	NPD5763	Approved
0.6743	Remote Similarity	NPD7819	Suspended
0.6734	Remote Similarity	NPD7874	Approved
0.6734	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7610	Discontinued
0.6726	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6823	Phase 2
0.6717	Remote Similarity	NPD7701	Phase 2
0.6709	Remote Similarity	NPD7736	Approved
0.6701	Remote Similarity	NPD6777	Approved
0.6701	Remote Similarity	NPD6781	Approved
0.6701	Remote Similarity	NPD6779	Approved
0.6701	Remote Similarity	NPD6780	Approved
0.6701	Remote Similarity	NPD6778	Approved
0.6701	Remote Similarity	NPD6782	Approved
0.6701	Remote Similarity	NPD6776	Approved
0.67	Remote Similarity	NPD7783	Phase 2
0.67	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD4380	Phase 2
0.665	Remote Similarity	NPD7871	Phase 2
0.665	Remote Similarity	NPD7870	Phase 2
0.6648	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5951	Approved
0.6645	Remote Similarity	NPD8515	Approved
0.6645	Remote Similarity	NPD8516	Approved
0.6645	Remote Similarity	NPD8517	Approved
0.6645	Remote Similarity	NPD8513	Phase 3
0.6629	Remote Similarity	NPD7075	Discontinued
0.6627	Remote Similarity	NPD7003	Approved
0.6622	Remote Similarity	NPD6686	Approved
0.6617	Remote Similarity	NPD7801	Approved
0.6612	Remote Similarity	NPD3818	Discontinued
0.6609	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7680	Approved
0.659	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6190	Approved
0.6585	Remote Similarity	NPD4140	Approved
0.6584	Remote Similarity	NPD8462	Phase 1
0.6581	Remote Similarity	NPD7009	Phase 2
0.6577	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6674	Discontinued
0.6564	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6213	Phase 3
0.6562	Remote Similarity	NPD6212	Phase 3
0.6561	Remote Similarity	NPD8328	Phase 3
0.6554	Remote Similarity	NPD6685	Approved
0.6554	Remote Similarity	NPD6412	Phase 2
0.6548	Remote Similarity	NPD6005	Phase 3
0.6548	Remote Similarity	NPD6002	Phase 3
0.6548	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6004	Phase 3
0.6548	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7999	Approved
0.6524	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3751	Discontinued
0.6517	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6166	Phase 2
0.6503	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7768	Phase 2
0.6477	Remote Similarity	NPD6599	Discontinued
0.6467	Remote Similarity	NPD2182	Approved
0.6467	Remote Similarity	NPD7473	Discontinued
0.646	Remote Similarity	NPD3094	Phase 2
0.6456	Remote Similarity	NPD8404	Phase 2
0.6446	Remote Similarity	NPD5735	Approved
0.6446	Remote Similarity	NPD6355	Discontinued
0.6441	Remote Similarity	NPD7411	Suspended
0.6439	Remote Similarity	NPD7930	Approved
0.6433	Remote Similarity	NPD3750	Approved
0.6429	Remote Similarity	NPD6959	Discontinued
0.6425	Remote Similarity	NPD5402	Approved
0.6424	Remote Similarity	NPD7714	Approved
0.6424	Remote Similarity	NPD7715	Approved
0.6424	Remote Similarity	NPD8032	Phase 2
0.642	Remote Similarity	NPD6085	Phase 2
0.642	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6653	Approved
0.6404	Remote Similarity	NPD6801	Discontinued
0.64	Remote Similarity	NPD5403	Approved
0.6393	Remote Similarity	NPD6232	Discontinued
0.6393	Remote Similarity	NPD3787	Discontinued
0.6392	Remote Similarity	NPD6370	Approved
0.6387	Remote Similarity	NPD7115	Discovery

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