NPASS Compound

Structure

NPC470038 OpenBabel07101719162D 36 40 0 0 1 0 0 0 0 0999 V2000 -3.4641 -4.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2679 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 3 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 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 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2321 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 5 29 1 0 0 0 0 7 36 1 0 0 0 0 8 10 1 0 0 0 0 8 26 1 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 29 1 0 0 0 0 11 30 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 28 1 0 0 0 0 15 22 1 0 0 0 0 15 26 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 31 2 0 0 0 0 19 24 2 0 0 0 0 19 32 1 0 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 21 26 1 6 0 0 0 21 30 1 0 0 0 0 22 28 1 0 0 0 0 22 33 2 0 0 0 0 24 34 1 0 0 0 0 25 28 1 0 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 2 1 1 0 0 0 27 3 1 1 0 0 0 28 4 1 1 0 0 0 29 30 1 1 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.28
Volume:	521.576
LogP:	3.491
LogD:	2.987
LogS:	-4.455
# Rotatable Bonds:	2
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	4.96
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.22
MDCK Permeability:	1.8639177142176777e-05
Pgp-inhibitor:	0.608
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.245
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.358
Plasma Protein Binding (PPB):	93.51119232177734%
Volume Distribution (VD):	0.915
Pgp-substrate:	9.776090621948242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.763
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.309
CYP2D6-inhibitor:	0.215
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.834

ADMET: Excretion

Clearance (CL):	15.075
Half-life (T1/2):	0.378

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.136
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.83
Skin Sensitization:	0.09
Carcinogencity:	0.58
Eye Corrosion:	0.004
Eye Irritation:	0.34
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC470038

Natural Product ID:	NPC470038
*Common Name:**	Blepharodol
IUPAC Name:	methyl (2S,4aS,6aR,6aR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-3,8-dioxo-4,5,6,6b,7,13,14,14b-octahydro-1H-picene-2-carboxylate
Synonyms:	Blepharodol
Standard InCHIKey:	IWTGNLXWDMHZOI-QYOTWRPRSA-N
Standard InCHI:	InChI=1S/C30H40O6/c1-16-23-17(12-19(32)24(16)34)27(3)9-11-30(6)21-14-28(4,25(35)36-7)22(33)15-26(21,2)8-10-29(30,5)20(27)13-18(23)31/h12,20-21,32,34H,8-11,13-15H2,1-7H3/t20?,21-,26+,27+,28+,29-,30+/m1/s1
SMILES:	COC(=O)[C@@]1(C)C[C@@H]2[C@@](CC1=O)(C)CC[C@]1([C@@]2(C)CC[C@@]2(C1CC(=O)c1c2cc(O)c(c1C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651348
PubChem CID:	53326085
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO25224	Maytenus retusa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090801]
NPO25224	Maytenus retusa	Species	Celastraceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	7.0	%	PMID[521356]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	8.0	%	PMID[521356]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	15.0	%	PMID[521356]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	100.0	%	PMID[521356]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	79.0	%	PMID[521356]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	69.0	%	PMID[521356]

☑ 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 NPC470038 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	350
0.1-0.2	1528
0.2-0.3	2993
0.3-0.4	7220
0.4-0.5	10167
0.5-0.6	8408
0.6-0.7	9360
0.7-0.8	2526
0.8-0.85	123
0.85-0.9	12
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC470037
0.964	High Similarity	NPC184935
0.9496	High Similarity	NPC470035
0.942	High Similarity	NPC49911
0.9306	High Similarity	NPC10842
0.9281	High Similarity	NPC277559
0.8993	High Similarity	NPC476282
0.8897	High Similarity	NPC199936
0.8889	High Similarity	NPC185617
0.8849	High Similarity	NPC243305
0.8776	High Similarity	NPC75295
0.8723	High Similarity	NPC111845
0.8681	High Similarity	NPC469681
0.8681	High Similarity	NPC469680
0.8681	High Similarity	NPC471974
0.8671	High Similarity	NPC7464
0.8667	High Similarity	NPC142654
0.8649	High Similarity	NPC258856
0.8601	High Similarity	NPC103082
0.8601	High Similarity	NPC43353
0.8601	High Similarity	NPC153088
0.8592	High Similarity	NPC138472
0.8562	High Similarity	NPC471853
0.8552	High Similarity	NPC473479
0.8552	High Similarity	NPC477849
0.8552	High Similarity	NPC165191
0.8552	High Similarity	NPC469857
0.8552	High Similarity	NPC157284
0.8552	High Similarity	NPC51531
0.8552	High Similarity	NPC46242
0.8552	High Similarity	NPC5014
0.8552	High Similarity	NPC289358
0.8552	High Similarity	NPC42384
0.8552	High Similarity	NPC245760
0.8552	High Similarity	NPC28592
0.8552	High Similarity	NPC114333
0.8552	High Similarity	NPC297797
0.8552	High Similarity	NPC473779
0.8552	High Similarity	NPC149773
0.8552	High Similarity	NPC23667
0.8552	High Similarity	NPC91887
0.8552	High Similarity	NPC50615
0.8531	High Similarity	NPC293454
0.8493	Intermediate Similarity	NPC294330
0.8456	Intermediate Similarity	NPC8493
0.8456	Intermediate Similarity	NPC469375
0.8456	Intermediate Similarity	NPC144247
0.8456	Intermediate Similarity	NPC294679
0.8456	Intermediate Similarity	NPC145301
0.8446	Intermediate Similarity	NPC469447
0.8446	Intermediate Similarity	NPC30846
0.8446	Intermediate Similarity	NPC248068
0.8446	Intermediate Similarity	NPC469855
0.8446	Intermediate Similarity	NPC477873
0.8446	Intermediate Similarity	NPC471971
0.8446	Intermediate Similarity	NPC471972
0.8435	Intermediate Similarity	NPC476534
0.8435	Intermediate Similarity	NPC473527
0.8431	Intermediate Similarity	NPC124842
0.8425	Intermediate Similarity	NPC230811
0.8356	Intermediate Similarity	NPC471152
0.8355	Intermediate Similarity	NPC264229
0.8355	Intermediate Similarity	NPC46549
0.8345	Intermediate Similarity	NPC258502
0.8344	Intermediate Similarity	NPC471970
0.8344	Intermediate Similarity	NPC143685
0.8344	Intermediate Similarity	NPC273798
0.8333	Intermediate Similarity	NPC309169
0.8333	Intermediate Similarity	NPC469854
0.8333	Intermediate Similarity	NPC4170
0.8333	Intermediate Similarity	NPC53520
0.8333	Intermediate Similarity	NPC196941
0.8333	Intermediate Similarity	NPC294226
0.8333	Intermediate Similarity	NPC469856
0.8323	Intermediate Similarity	NPC62051
0.8322	Intermediate Similarity	NPC291001
0.8299	Intermediate Similarity	NPC416
0.8299	Intermediate Similarity	NPC61398
0.8298	Intermediate Similarity	NPC69424
0.8298	Intermediate Similarity	NPC176130
0.8298	Intermediate Similarity	NPC78364
0.8298	Intermediate Similarity	NPC84672
0.8289	Intermediate Similarity	NPC52692
0.8288	Intermediate Similarity	NPC472308
0.8278	Intermediate Similarity	NPC8102
0.8278	Intermediate Similarity	NPC66894
0.8276	Intermediate Similarity	NPC202225
0.8252	Intermediate Similarity	NPC108129
0.8239	Intermediate Similarity	NPC266365
0.8235	Intermediate Similarity	NPC132810
0.8224	Intermediate Similarity	NPC474991
0.8217	Intermediate Similarity	NPC471968
0.8212	Intermediate Similarity	NPC126707
0.82	Intermediate Similarity	NPC85310
0.8194	Intermediate Similarity	NPC18798
0.8194	Intermediate Similarity	NPC471851
0.8182	Intermediate Similarity	NPC276238
0.8182	Intermediate Similarity	NPC303910
0.8182	Intermediate Similarity	NPC237441
0.817	Intermediate Similarity	NPC470757
0.8169	Intermediate Similarity	NPC72667
0.8158	Intermediate Similarity	NPC68441
0.8158	Intermediate Similarity	NPC84786
0.8153	Intermediate Similarity	NPC472807
0.8133	Intermediate Similarity	NPC2681
0.8133	Intermediate Similarity	NPC92079
0.8133	Intermediate Similarity	NPC272907
0.8129	Intermediate Similarity	NPC473579
0.8129	Intermediate Similarity	NPC475454
0.8129	Intermediate Similarity	NPC48949
0.8129	Intermediate Similarity	NPC473680
0.8129	Intermediate Similarity	NPC475311
0.8125	Intermediate Similarity	NPC117609
0.8113	Intermediate Similarity	NPC326084
0.8112	Intermediate Similarity	NPC234175
0.8112	Intermediate Similarity	NPC229894
0.811	Intermediate Similarity	NPC472803
0.8108	Intermediate Similarity	NPC475957
0.8108	Intermediate Similarity	NPC147418
0.8105	Intermediate Similarity	NPC246229
0.8105	Intermediate Similarity	NPC191899
0.8105	Intermediate Similarity	NPC476535
0.8105	Intermediate Similarity	NPC58752
0.8099	Intermediate Similarity	NPC254492
0.8095	Intermediate Similarity	NPC72918
0.8095	Intermediate Similarity	NPC477596
0.8089	Intermediate Similarity	NPC305710
0.8085	Intermediate Similarity	NPC199273
0.8082	Intermediate Similarity	NPC49742
0.8082	Intermediate Similarity	NPC474715
0.8082	Intermediate Similarity	NPC475457
0.8082	Intermediate Similarity	NPC475346
0.8082	Intermediate Similarity	NPC78307
0.8082	Intermediate Similarity	NPC18982
0.8082	Intermediate Similarity	NPC475627
0.8082	Intermediate Similarity	NPC477139
0.8079	Intermediate Similarity	NPC239136
0.8079	Intermediate Similarity	NPC169214
0.8079	Intermediate Similarity	NPC141817
0.8079	Intermediate Similarity	NPC11314
0.8079	Intermediate Similarity	NPC192597
0.8079	Intermediate Similarity	NPC19631
0.8079	Intermediate Similarity	NPC176030
0.8079	Intermediate Similarity	NPC229218
0.8077	Intermediate Similarity	NPC35
0.8077	Intermediate Similarity	NPC144283
0.8075	Intermediate Similarity	NPC315772
0.8067	Intermediate Similarity	NPC3218
0.8067	Intermediate Similarity	NPC315578
0.8067	Intermediate Similarity	NPC304110
0.8067	Intermediate Similarity	NPC225243
0.8067	Intermediate Similarity	NPC27518
0.8065	Intermediate Similarity	NPC474310
0.8065	Intermediate Similarity	NPC327962
0.8065	Intermediate Similarity	NPC303989
0.8063	Intermediate Similarity	NPC475449
0.8056	Intermediate Similarity	NPC171460
0.8056	Intermediate Similarity	NPC117899
0.8054	Intermediate Similarity	NPC206207
0.8054	Intermediate Similarity	NPC4214
0.8054	Intermediate Similarity	NPC141368
0.8054	Intermediate Similarity	NPC182249
0.8052	Intermediate Similarity	NPC127046
0.8052	Intermediate Similarity	NPC5568
0.805	Intermediate Similarity	NPC317580
0.8039	Intermediate Similarity	NPC160777
0.8039	Intermediate Similarity	NPC73416
0.8039	Intermediate Similarity	NPC12402
0.8038	Intermediate Similarity	NPC318270
0.8037	Intermediate Similarity	NPC200726
0.8027	Intermediate Similarity	NPC472262
0.8027	Intermediate Similarity	NPC161964
0.8027	Intermediate Similarity	NPC287604
0.8027	Intermediate Similarity	NPC477594
0.8027	Intermediate Similarity	NPC204582
0.8026	Intermediate Similarity	NPC474203
0.8026	Intermediate Similarity	NPC295712
0.8026	Intermediate Similarity	NPC174905
0.8026	Intermediate Similarity	NPC313047
0.8026	Intermediate Similarity	NPC25491
0.8026	Intermediate Similarity	NPC451542
0.8026	Intermediate Similarity	NPC100242
0.8026	Intermediate Similarity	NPC293545
0.8026	Intermediate Similarity	NPC66593
0.8025	Intermediate Similarity	NPC164912
0.8014	Intermediate Similarity	NPC198014
0.8013	Intermediate Similarity	NPC280295
0.8013	Intermediate Similarity	NPC118033
0.8013	Intermediate Similarity	NPC315520
0.8013	Intermediate Similarity	NPC472904
0.8013	Intermediate Similarity	NPC205766
0.8	Intermediate Similarity	NPC155192
0.8	Intermediate Similarity	NPC249340
0.8	Intermediate Similarity	NPC162935
0.8	Intermediate Similarity	NPC473591
0.8	Intermediate Similarity	NPC26924
0.8	Intermediate Similarity	NPC271494
0.8	Intermediate Similarity	NPC471907
0.7988	Intermediate Similarity	NPC472622
0.7988	Intermediate Similarity	NPC177362

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 NPC470038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	943
0.2-0.3	1611
0.3-0.4	2795
0.4-0.5	2129
0.5-0.6	977
0.6-0.7	356
0.7-0.8	30
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
0.8503	High Similarity	NPD8166	Discontinued
0.8158	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7458	Discontinued
0.7895	Intermediate Similarity	NPD7003	Approved
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7818	Intermediate Similarity	NPD7473	Discontinued
0.7748	Intermediate Similarity	NPD5404	Approved
0.7748	Intermediate Similarity	NPD5406	Approved
0.7748	Intermediate Similarity	NPD5408	Approved
0.7748	Intermediate Similarity	NPD5405	Approved
0.7688	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6232	Discontinued
0.7534	Intermediate Similarity	NPD1470	Approved
0.7533	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.7483	Intermediate Similarity	NPD3019	Approved
0.7467	Intermediate Similarity	NPD6663	Approved
0.7432	Intermediate Similarity	NPD5736	Approved
0.7361	Intermediate Similarity	NPD2932	Approved
0.7342	Intermediate Similarity	NPD3300	Phase 2
0.7338	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8150	Discontinued
0.7262	Intermediate Similarity	NPD6959	Discontinued
0.7244	Intermediate Similarity	NPD2346	Discontinued
0.7229	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2799	Discontinued
0.7212	Intermediate Similarity	NPD7819	Suspended
0.7205	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.7197	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7115	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5844	Phase 1
0.7108	Intermediate Similarity	NPD1465	Phase 2
0.7108	Intermediate Similarity	NPD2801	Approved
0.7095	Intermediate Similarity	NPD9269	Phase 2
0.7083	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3026	Approved
0.7075	Intermediate Similarity	NPD3023	Approved
0.7067	Intermediate Similarity	NPD1164	Approved
0.7063	Intermediate Similarity	NPD5951	Approved
0.7059	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD3025	Approved
0.7055	Intermediate Similarity	NPD3024	Approved
0.7048	Intermediate Similarity	NPD1934	Approved
0.7044	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6166	Phase 2
0.7035	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD4628	Phase 3
0.6987	Remote Similarity	NPD6651	Approved
0.6982	Remote Similarity	NPD7075	Discontinued
0.6975	Remote Similarity	NPD1511	Approved
0.6971	Remote Similarity	NPD7074	Phase 3
0.697	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8127	Discontinued
0.6957	Remote Similarity	NPD6190	Approved
0.6954	Remote Similarity	NPD7228	Approved
0.695	Remote Similarity	NPD3021	Approved
0.695	Remote Similarity	NPD3022	Approved
0.6941	Remote Similarity	NPD6234	Discontinued
0.6936	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3882	Suspended
0.6923	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD7054	Approved
0.6905	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8032	Phase 2
0.6892	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4626	Approved
0.689	Remote Similarity	NPD1512	Approved
0.6886	Remote Similarity	NPD7411	Suspended
0.6883	Remote Similarity	NPD7008	Discontinued
0.6883	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7472	Approved
0.6871	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3972	Approved
0.6864	Remote Similarity	NPD3817	Phase 2
0.6863	Remote Similarity	NPD9494	Approved
0.6859	Remote Similarity	NPD3620	Phase 2
0.6859	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4060	Phase 1
0.6845	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD2313	Discontinued
0.6832	Remote Similarity	NPD2800	Approved
0.6829	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4380	Phase 2
0.6826	Remote Similarity	NPD7028	Phase 2
0.6826	Remote Similarity	NPD6599	Discontinued
0.6824	Remote Similarity	NPD9268	Approved
0.6823	Remote Similarity	NPD8151	Discontinued
0.6821	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2344	Approved
0.681	Remote Similarity	NPD7236	Approved
0.6802	Remote Similarity	NPD5494	Approved
0.68	Remote Similarity	NPD3092	Approved
0.68	Remote Similarity	NPD1281	Approved
0.6798	Remote Similarity	NPD7251	Discontinued
0.6797	Remote Similarity	NPD2798	Approved
0.679	Remote Similarity	NPD3750	Approved
0.679	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8320	Phase 1
0.6789	Remote Similarity	NPD8319	Approved
0.6784	Remote Similarity	NPD3749	Approved
0.6779	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3818	Discontinued
0.6761	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3091	Approved
0.675	Remote Similarity	NPD6099	Approved
0.675	Remote Similarity	NPD6100	Approved
0.6746	Remote Similarity	NPD6801	Discontinued
0.6742	Remote Similarity	NPD6797	Phase 2
0.6737	Remote Similarity	NPD7435	Discontinued
0.6735	Remote Similarity	NPD9493	Approved
0.6732	Remote Similarity	NPD3094	Phase 2
0.6727	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4966	Approved
0.6725	Remote Similarity	NPD4965	Approved
0.6725	Remote Similarity	NPD4967	Phase 2
0.6709	Remote Similarity	NPD447	Suspended
0.6703	Remote Similarity	NPD8434	Phase 2
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD4110	Phase 3
0.6687	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD7808	Phase 3
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD3455	Phase 2
0.6649	Remote Similarity	NPD7699	Phase 2
0.6649	Remote Similarity	NPD7700	Phase 2
0.6647	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD825	Approved
0.6646	Remote Similarity	NPD1240	Approved
0.6646	Remote Similarity	NPD2979	Phase 3
0.6646	Remote Similarity	NPD2309	Approved
0.6646	Remote Similarity	NPD826	Approved
0.6644	Remote Similarity	NPD9545	Approved
0.6629	Remote Similarity	NPD5710	Approved
0.6629	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5711	Approved
0.6627	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3268	Approved
0.6613	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6212	Phase 3
0.6613	Remote Similarity	NPD6213	Phase 3
0.6611	Remote Similarity	NPD7685	Pre-registration
0.6607	Remote Similarity	NPD7239	Suspended
0.6605	Remote Similarity	NPD7266	Discontinued
0.6604	Remote Similarity	NPD6355	Discontinued
0.66	Remote Similarity	NPD1651	Approved
0.66	Remote Similarity	NPD5691	Approved
0.6599	Remote Similarity	NPD2629	Approved
0.6582	Remote Similarity	NPD7961	Discontinued
0.6581	Remote Similarity	NPD257	Approved
0.6581	Remote Similarity	NPD258	Approved
0.6579	Remote Similarity	NPD6779	Approved
0.6579	Remote Similarity	NPD6781	Approved
0.6579	Remote Similarity	NPD6780	Approved
0.6579	Remote Similarity	NPD6782	Approved
0.6579	Remote Similarity	NPD6776	Approved
0.6579	Remote Similarity	NPD6778	Approved
0.6579	Remote Similarity	NPD6777	Approved
0.6575	Remote Similarity	NPD4954	Approved
0.6575	Remote Similarity	NPD36	Approved
0.6575	Remote Similarity	NPD7635	Approved
0.6575	Remote Similarity	NPD4955	Approved
0.6575	Remote Similarity	NPD5028	Approved
0.6575	Remote Similarity	NPD5026	Approved
0.6575	Remote Similarity	NPD5034	Approved
0.6573	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7199	Phase 2
0.6566	Remote Similarity	NPD6799	Approved
0.6558	Remote Similarity	NPD1876	Approved
0.6556	Remote Similarity	NPD4059	Approved
0.6556	Remote Similarity	NPD3095	Discontinued
0.6545	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2438	Suspended
0.6541	Remote Similarity	NPD4140	Approved
0.6531	Remote Similarity	NPD7875	Clinical (unspecified phase)

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