NPASS Compound

Structure

NPC472372 OpenBabel07101719252D 42 45 0 0 1 0 0 0 0 0999 V2000 -0.8111 -2.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2425 1.0290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8025 -3.0849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4559 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8025 2.1483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8312 -1.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1896 -0.8143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5701 -0.7430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2516 3.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1294 2.1247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5086 3.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2641 1.7662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6433 3.2649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6222 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8111 0.4683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9707 -1.1531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8111 -1.4048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5018 0.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8740 -3.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8858 1.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8740 2.2705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5988 -1.5988 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6222 -0.9366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9275 -0.3842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2611 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6622 -1.5988 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5988 0.6622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6622 0.6622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6558 1.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2611 -0.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5156 -4.0724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2442 2.5150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5156 3.1358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4333 -1.4048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9128 2.5481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3038 -2.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9572 1.5275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3038 1.5275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5336 1.0494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 32 1 0 0 0 0 7 32 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 33 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 17 27 1 0 0 0 0 18 25 1 0 0 0 0 18 26 2 0 0 0 0 19 34 2 0 0 0 0 19 39 1 0 0 0 0 20 35 2 0 0 0 0 20 40 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 31 1 0 0 0 0 23 16 1 1 0 0 0 23 28 1 0 0 0 0 23 32 1 0 0 0 0 24 37 1 1 0 0 0 25 42 1 6 0 0 0 26 29 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 33 1 6 0 0 0 28 39 1 1 0 0 0 29 30 1 0 0 0 0 29 40 1 6 0 0 0 30 33 1 1 0 0 0 30 41 1 0 0 0 0 31 38 2 0 0 0 0 31 42 1 0 0 0 0 33 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.28
Volume:	600.482
LogP:	4.16
LogD:	3.416
LogS:	-4.501
# Rotatable Bonds:	9
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	5.442
Fsp3:	0.576
Lipinski Rule-of-5:	Accepted
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:	-5.082
MDCK Permeability:	8.086234447546303e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	81.48604583740234%
Volume Distribution (VD):	2.593
Pgp-substrate:	14.567828178405762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.57
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	4.229
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.229
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.678
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.091
Carcinogencity:	0.058
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC472372

Natural Product ID:	NPC472372
*Common Name:**	RVJHLRGBPGMFRC-OMVMMUDDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RVJHLRGBPGMFRC-OMVMMUDDSA-N
Standard InCHI:	InChI=1S/C33H42O9/c1-17-24(37)14-15-33(8)27(17)28(39-19(3)34)23-16-25(42-31(38)22-12-10-9-11-13-22)18(2)26(32(23,6)7)29(40-20(4)35)30(33)41-21(5)36/h9-13,23-25,27-30,37H,1,14-16H2,2-8H3/t23-,24-,25-,27-,28+,29+,30-,33+/m0/s1
SMILES:	CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)c3ccccc3)C[C@H](C2(C)C)[C@H]([C@H]2[C@@]([C@H]1OC(=O)C)(C)CC[C@@H](C2=C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL339622
PubChem CID:	44351349
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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
Others	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Control	=	185.0	%	PMID[453558]
NPT2	Others	Unspecified	Control	=	643.0	%	PMID[453558]
NPT2	Others	Unspecified	Activity	=	87.0	%	PMID[453559]

☑ 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 NPC472372 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	268
0.1-0.2	1002
0.2-0.3	2139
0.3-0.4	4716
0.4-0.5	9115
0.5-0.6	12277
0.6-0.7	11318
0.7-0.8	1599
0.8-0.85	217
0.85-0.9	34
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472374
0.9478	High Similarity	NPC34012
0.9385	High Similarity	NPC472394
0.9338	High Similarity	NPC38696
0.9231	High Similarity	NPC472388
0.9185	High Similarity	NPC472547
0.9173	High Similarity	NPC477893
0.9154	High Similarity	NPC225103
0.9084	High Similarity	NPC473443
0.907	High Similarity	NPC275576
0.9065	High Similarity	NPC474935
0.9062	High Similarity	NPC472373
0.9044	High Similarity	NPC90614
0.9037	High Similarity	NPC39549
0.903	High Similarity	NPC477896
0.9	High Similarity	NPC169913
0.9	High Similarity	NPC217918
0.8993	High Similarity	NPC472556
0.8986	High Similarity	NPC477894
0.8984	High Similarity	NPC12016
0.8978	High Similarity	NPC41481
0.8978	High Similarity	NPC87448
0.8978	High Similarity	NPC27377
0.8978	High Similarity	NPC97947
0.8978	High Similarity	NPC291599
0.8978	High Similarity	NPC118080
0.8978	High Similarity	NPC472576
0.8978	High Similarity	NPC16912
0.8971	High Similarity	NPC472395
0.8971	High Similarity	NPC472371
0.8963	High Similarity	NPC472545
0.8963	High Similarity	NPC472551
0.8955	High Similarity	NPC48929
0.8947	High Similarity	NPC80599
0.8944	High Similarity	NPC197037
0.8923	High Similarity	NPC45821
0.8913	High Similarity	NPC192658
0.8913	High Similarity	NPC472546
0.8905	High Similarity	NPC100913
0.8905	High Similarity	NPC171207
0.8905	High Similarity	NPC87934
0.8905	High Similarity	NPC275592
0.8905	High Similarity	NPC97667
0.8905	High Similarity	NPC162613
0.8873	High Similarity	NPC91730
0.8857	High Similarity	NPC177940
0.8857	High Similarity	NPC473088
0.8857	High Similarity	NPC472572
0.8857	High Similarity	NPC476973
0.8857	High Similarity	NPC171525
0.8857	High Similarity	NPC184817
0.8857	High Similarity	NPC96903
0.8857	High Similarity	NPC472571
0.8857	High Similarity	NPC200471
0.8857	High Similarity	NPC472575
0.8857	High Similarity	NPC471104
0.8857	High Similarity	NPC470157
0.8857	High Similarity	NPC470159
0.8857	High Similarity	NPC70403
0.8857	High Similarity	NPC469349
0.8857	High Similarity	NPC29704
0.8857	High Similarity	NPC472568
0.8857	High Similarity	NPC174982
0.8857	High Similarity	NPC158663
0.8849	High Similarity	NPC163087
0.8846	High Similarity	NPC471758
0.8841	High Similarity	NPC224491
0.8832	High Similarity	NPC9905
0.8819	High Similarity	NPC11588
0.8819	High Similarity	NPC248265
0.8819	High Similarity	NPC229545
0.8819	High Similarity	NPC134685
0.8806	High Similarity	NPC471880
0.8806	High Similarity	NPC209851
0.8794	High Similarity	NPC473602
0.8788	High Similarity	NPC195224
0.8786	High Similarity	NPC472573
0.8786	High Similarity	NPC95810
0.8786	High Similarity	NPC472570
0.8786	High Similarity	NPC475122
0.8786	High Similarity	NPC25768
0.8786	High Similarity	NPC472569
0.8786	High Similarity	NPC57628
0.8786	High Similarity	NPC470152
0.8786	High Similarity	NPC11685
0.8786	High Similarity	NPC241951
0.8786	High Similarity	NPC188865
0.8786	High Similarity	NPC95265
0.8786	High Similarity	NPC34943
0.8786	High Similarity	NPC70716
0.8786	High Similarity	NPC125106
0.8786	High Similarity	NPC475759
0.8786	High Similarity	NPC163719
0.8786	High Similarity	NPC476974
0.8769	High Similarity	NPC469742
0.8768	High Similarity	NPC475400
0.8759	High Similarity	NPC259144
0.8759	High Similarity	NPC114357
0.8759	High Similarity	NPC21410
0.8759	High Similarity	NPC473670
0.8759	High Similarity	NPC155329
0.875	High Similarity	NPC291638
0.875	High Similarity	NPC17877
0.875	High Similarity	NPC472577
0.875	High Similarity	NPC195647
0.875	High Similarity	NPC473399
0.875	High Similarity	NPC473216
0.875	High Similarity	NPC66761
0.8723	High Similarity	NPC125882
0.8714	High Similarity	NPC91703
0.8714	High Similarity	NPC95449
0.8712	High Similarity	NPC473220
0.8712	High Similarity	NPC470753
0.8705	High Similarity	NPC266374
0.869	High Similarity	NPC219419
0.8681	High Similarity	NPC470153
0.8676	High Similarity	NPC203486
0.8676	High Similarity	NPC474608
0.8671	High Similarity	NPC476975
0.8671	High Similarity	NPC92293
0.8671	High Similarity	NPC471101
0.8671	High Similarity	NPC266265
0.8671	High Similarity	NPC301556
0.8671	High Similarity	NPC270590
0.8662	High Similarity	NPC240115
0.8662	High Similarity	NPC20255
0.8657	High Similarity	NPC147561
0.8643	High Similarity	NPC182869
0.8636	High Similarity	NPC470765
0.8633	High Similarity	NPC473109
0.8633	High Similarity	NPC473081
0.8633	High Similarity	NPC477904
0.8633	High Similarity	NPC473112
0.8633	High Similarity	NPC473758
0.8633	High Similarity	NPC211137
0.8633	High Similarity	NPC473060
0.8633	High Similarity	NPC4341
0.8633	High Similarity	NPC184747
0.8633	High Similarity	NPC48017
0.8633	High Similarity	NPC476094
0.8633	High Similarity	NPC183270
0.8633	High Similarity	NPC43241
0.8633	High Similarity	NPC473613
0.8633	High Similarity	NPC473085
0.8633	High Similarity	NPC200592
0.8633	High Similarity	NPC147880
0.8621	High Similarity	NPC472548
0.8611	High Similarity	NPC7095
0.8611	High Similarity	NPC473214
0.8611	High Similarity	NPC470245
0.8601	High Similarity	NPC281717
0.8601	High Similarity	NPC473760
0.8594	High Similarity	NPC89324
0.8593	High Similarity	NPC72915
0.8593	High Similarity	NPC472418
0.8592	High Similarity	NPC311825
0.8592	High Similarity	NPC92867
0.8592	High Similarity	NPC127857
0.8582	High Similarity	NPC93632
0.8582	High Similarity	NPC477468
0.8571	High Similarity	NPC473423
0.8561	High Similarity	NPC475652
0.8561	High Similarity	NPC214550
0.8561	High Similarity	NPC210591
0.8542	High Similarity	NPC250046
0.8542	High Similarity	NPC60509
0.8542	High Similarity	NPC473215
0.8542	High Similarity	NPC81698
0.854	High Similarity	NPC126516
0.8538	High Similarity	NPC300827
0.8538	High Similarity	NPC473439
0.8531	High Similarity	NPC48599
0.8531	High Similarity	NPC312393
0.8531	High Similarity	NPC209592
0.8503	High Similarity	NPC472549
0.8493	Intermediate Similarity	NPC145649
0.8493	Intermediate Similarity	NPC469648
0.8493	Intermediate Similarity	NPC233581
0.8493	Intermediate Similarity	NPC138641
0.8493	Intermediate Similarity	NPC477905
0.8493	Intermediate Similarity	NPC469647
0.8493	Intermediate Similarity	NPC283875
0.8493	Intermediate Similarity	NPC327962
0.8493	Intermediate Similarity	NPC22571
0.8489	Intermediate Similarity	NPC183122
0.8489	Intermediate Similarity	NPC283375
0.8483	Intermediate Similarity	NPC112216
0.8483	Intermediate Similarity	NPC165260
0.8483	Intermediate Similarity	NPC161239
0.8483	Intermediate Similarity	NPC198455
0.8483	Intermediate Similarity	NPC469448
0.8473	Intermediate Similarity	NPC473749
0.8472	Intermediate Similarity	NPC132652
0.8456	Intermediate Similarity	NPC472361
0.8451	Intermediate Similarity	NPC270498
0.8451	Intermediate Similarity	NPC147217
0.8451	Intermediate Similarity	NPC246480
0.8451	Intermediate Similarity	NPC473673
0.8451	Intermediate Similarity	NPC475429
0.8451	Intermediate Similarity	NPC139067

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 NPC472372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	730
0.2-0.3	1410
0.3-0.4	2601
0.4-0.5	2278
0.5-0.6	1405
0.6-0.7	461
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8116	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD7236	Approved
0.7987	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7239	Suspended
0.7863	Intermediate Similarity	NPD2629	Approved
0.784	Intermediate Similarity	NPD8368	Discontinued
0.7823	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD7799	Discontinued
0.773	Intermediate Similarity	NPD7008	Discontinued
0.7711	Intermediate Similarity	NPD8434	Phase 2
0.7697	Intermediate Similarity	NPD8407	Phase 2
0.7674	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD8361	Approved
0.7619	Intermediate Similarity	NPD8360	Approved
0.7605	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5951	Approved
0.7584	Intermediate Similarity	NPD8166	Discontinued
0.7515	Intermediate Similarity	NPD8435	Approved
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7468	Intermediate Similarity	NPD7058	Phase 2
0.7468	Intermediate Similarity	NPD7057	Phase 3
0.7424	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4198	Discontinued
0.7405	Intermediate Similarity	NPD2182	Approved
0.7391	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7741	Discontinued
0.7356	Intermediate Similarity	NPD8485	Approved
0.7338	Intermediate Similarity	NPD6273	Approved
0.731	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7961	Discontinued
0.7237	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7003	Approved
0.7233	Intermediate Similarity	NPD7819	Suspended
0.7232	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8150	Discontinued
0.7171	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6287	Discontinued
0.7143	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD5126	Approved
0.7143	Intermediate Similarity	NPD5125	Phase 3
0.7133	Intermediate Similarity	NPD7305	Phase 1
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7122	Intermediate Similarity	NPD9545	Approved
0.7118	Intermediate Similarity	NPD8313	Approved
0.7118	Intermediate Similarity	NPD8312	Approved
0.7103	Intermediate Similarity	NPD5736	Approved
0.7099	Intermediate Similarity	NPD164	Approved
0.7099	Intermediate Similarity	NPD7075	Discontinued
0.7092	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3226	Approved
0.7063	Intermediate Similarity	NPD37	Approved
0.7059	Intermediate Similarity	NPD6858	Approved
0.7059	Intermediate Similarity	NPD7094	Approved
0.7054	Intermediate Similarity	NPD1238	Approved
0.7051	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4380	Phase 2
0.7039	Intermediate Similarity	NPD2346	Discontinued
0.7037	Intermediate Similarity	NPD4965	Approved
0.7037	Intermediate Similarity	NPD4967	Phase 2
0.7037	Intermediate Similarity	NPD4966	Approved
0.7023	Intermediate Similarity	NPD1930	Approved
0.7023	Intermediate Similarity	NPD1929	Approved
0.7023	Intermediate Similarity	NPD6647	Phase 2
0.7023	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3750	Approved
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD6764	Approved
0.7	Intermediate Similarity	NPD6765	Approved
0.6974	Remote Similarity	NPD2935	Discontinued
0.697	Remote Similarity	NPD1237	Approved
0.697	Remote Similarity	NPD5909	Discontinued
0.6968	Remote Similarity	NPD6190	Approved
0.6968	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6801	Discontinued
0.6937	Remote Similarity	NPD6599	Discontinued
0.6936	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7768	Phase 2
0.6933	Remote Similarity	NPD6355	Discontinued
0.6932	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6232	Discontinued
0.6928	Remote Similarity	NPD7266	Discontinued
0.6923	Remote Similarity	NPD2066	Phase 3
0.6914	Remote Similarity	NPD8455	Phase 2
0.6914	Remote Similarity	NPD5760	Phase 2
0.6914	Remote Similarity	NPD5761	Phase 2
0.6913	Remote Similarity	NPD7715	Approved
0.6913	Remote Similarity	NPD7714	Approved
0.6908	Remote Similarity	NPD2799	Discontinued
0.6887	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6010	Discontinued
0.6871	Remote Similarity	NPD5402	Approved
0.6871	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5404	Approved
0.6863	Remote Similarity	NPD5406	Approved
0.6863	Remote Similarity	NPD5408	Approved
0.6863	Remote Similarity	NPD5405	Approved
0.6863	Remote Similarity	NPD2438	Suspended
0.6861	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5403	Approved
0.6848	Remote Similarity	NPD6234	Discontinued
0.6846	Remote Similarity	NPD2313	Discontinued
0.6839	Remote Similarity	NPD6784	Approved
0.6839	Remote Similarity	NPD6785	Approved
0.6838	Remote Similarity	NPD2067	Discontinued
0.6835	Remote Similarity	NPD2534	Approved
0.6835	Remote Similarity	NPD2532	Approved
0.6835	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2533	Approved
0.6821	Remote Similarity	NPD230	Phase 1
0.6818	Remote Similarity	NPD6002	Phase 3
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5762	Approved
0.6818	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6005	Phase 3
0.6818	Remote Similarity	NPD6004	Phase 3
0.6818	Remote Similarity	NPD5763	Approved
0.6818	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7610	Discontinued
0.6806	Remote Similarity	NPD4806	Approved
0.6806	Remote Similarity	NPD4807	Approved
0.6803	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6085	Phase 2
0.6802	Remote Similarity	NPD7685	Pre-registration
0.6802	Remote Similarity	NPD6559	Discontinued
0.68	Remote Similarity	NPD8032	Phase 2
0.68	Remote Similarity	NPD7713	Phase 3
0.6797	Remote Similarity	NPD3748	Approved
0.6795	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4110	Phase 3
0.6791	Remote Similarity	NPD5048	Discontinued
0.679	Remote Similarity	NPD7411	Suspended
0.6788	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2932	Approved
0.6783	Remote Similarity	NPD5306	Approved
0.6783	Remote Similarity	NPD5305	Approved
0.6781	Remote Similarity	NPD1283	Approved
0.6774	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7228	Approved
0.6759	Remote Similarity	NPD1608	Approved
0.6755	Remote Similarity	NPD2979	Phase 3
0.6755	Remote Similarity	NPD4140	Approved
0.6747	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6685	Approved
0.6735	Remote Similarity	NPD2797	Approved
0.6735	Remote Similarity	NPD1470	Approved
0.6733	Remote Similarity	NPD6798	Discontinued
0.6732	Remote Similarity	NPD7097	Phase 1
0.673	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5401	Approved
0.6725	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8462	Phase 1
0.6718	Remote Similarity	NPD9495	Approved
0.6711	Remote Similarity	NPD6832	Phase 2
0.6707	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1201	Approved
0.6689	Remote Similarity	NPD2798	Approved
0.6688	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD8651	Approved
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1934	Approved
0.6645	Remote Similarity	NPD1551	Phase 2
0.6645	Remote Similarity	NPD6100	Approved
0.6645	Remote Similarity	NPD6099	Approved
0.6645	Remote Similarity	NPD4060	Phase 1
0.6644	Remote Similarity	NPD3972	Approved
0.6643	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3268	Approved
0.6623	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4106	Approved
0.6621	Remote Similarity	NPD4136	Approved
0.6621	Remote Similarity	NPD4135	Approved
0.662	Remote Similarity	NPD9493	Approved
0.6613	Remote Similarity	NPD8320	Phase 1
0.6613	Remote Similarity	NPD8319	Approved
0.659	Remote Similarity	NPD7074	Phase 3
0.6589	Remote Similarity	NPD1088	Approved
0.6582	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7033	Discontinued

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