NPASS Compound

Structure

NPC473049 OpenBabel07101718202D 30 35 0 0 1 0 0 0 0 0999 V2000 0.7661 -2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9825 -4.4376 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 5.1962 -2.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 5.1962 -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 1.7321 -3.0000 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 -1.7321 -2.0000 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 4.2007 -1.7728 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 -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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8952 -2.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 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 5.8261 -3.3410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -2.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 17 2 0 0 0 0 6 18 2 0 0 0 0 7 11 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 24 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 26 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 6 0 0 0 19 26 1 0 0 0 0 20 24 1 6 0 0 0 20 26 1 0 0 0 0 21 23 1 6 0 0 0 21 25 1 0 0 0 0 22 24 1 6 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 23 1 1 6 0 0 0 24 2 1 1 0 0 0 25 3 1 6 0 0 0 25 30 1 0 0 0 0 26 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.26
Volume:	434.165
LogP:	5.159
LogD:	4.052
LogS:	-5.272
# Rotatable Bonds:	0
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	5.412
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	2.360810867685359e-05
Pgp-inhibitor:	0.105
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.099
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.464
Plasma Protein Binding (PPB):	94.7620849609375%
Volume Distribution (VD):	1.051
Pgp-substrate:	3.5449869632720947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.176
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.315
CYP2D6-substrate:	0.808
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.408

ADMET: Excretion

Clearance (CL):	9.948
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.669
Human Hepatotoxicity (H-HT):	0.557
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.914
Carcinogencity:	0.456
Eye Corrosion:	0.004
Eye Irritation:	0.113
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC473049

Natural Product ID:	NPC473049
*Common Name:**	CZBILTFRGJCVGE-BGLMPXDFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CZBILTFRGJCVGE-BGLMPXDFSA-N
Standard InCHI:	InChI=1S/C26H36O4/c1-23-11-7-20-24(2)9-4-10-26(20,15-29-22(24)28)19(23)8-12-25(3)21(23)14-16-13-17(27)5-6-18(16)30-25/h5-6,13,19-22,27-28H,4,7-12,14-15H2,1-3H3/t19-,20-,21-,22-,23+,24+,25-,26-/m0/s1
SMILES:	Oc1ccc2c(c1)C[C@@H]1[C@](O2)(C)CC[C@H]2[C@@]1(C)CC[C@@H]1[C@@]32CCC[C@@]1(C)[C@H](OC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608573
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33273	strongylophora strongilata	Species	n.a.	n.a.	n.a.	Iriomote Island	n.a.	PMID[26253631]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	11900.0	nM	PMID[506628]

☑ 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 NPC473049 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	442
0.1-0.2	1618
0.2-0.3	3465
0.3-0.4	8033
0.4-0.5	9403
0.5-0.6	9368
0.6-0.7	8887
0.7-0.8	1435
0.8-0.85	29
0.85-0.9	9
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472794
0.9776	High Similarity	NPC472792
0.9776	High Similarity	NPC472791
0.9545	High Similarity	NPC211352
0.9394	High Similarity	NPC153019
0.9179	High Similarity	NPC27578
0.9179	High Similarity	NPC289624
0.9173	High Similarity	NPC472793
0.9167	High Similarity	NPC47288
0.903	High Similarity	NPC473048
0.8963	High Similarity	NPC473047
0.8873	High Similarity	NPC474599
0.8864	High Similarity	NPC248557
0.8723	High Similarity	NPC79372
0.8723	High Similarity	NPC76312
0.8652	High Similarity	NPC265335
0.8643	High Similarity	NPC474610
0.8636	High Similarity	NPC475839
0.8467	Intermediate Similarity	NPC176590
0.8357	Intermediate Similarity	NPC321086
0.8357	Intermediate Similarity	NPC85595
0.8346	Intermediate Similarity	NPC474131
0.8345	Intermediate Similarity	NPC325003
0.8344	Intermediate Similarity	NPC475227
0.8344	Intermediate Similarity	NPC106669
0.8344	Intermediate Similarity	NPC200645
0.8333	Intermediate Similarity	NPC223912
0.8333	Intermediate Similarity	NPC164743
0.8322	Intermediate Similarity	NPC44452
0.8321	Intermediate Similarity	NPC128321
0.8299	Intermediate Similarity	NPC472457
0.8299	Intermediate Similarity	NPC90645
0.8298	Intermediate Similarity	NPC138940
0.8278	Intermediate Similarity	NPC476452
0.8278	Intermediate Similarity	NPC325860
0.8271	Intermediate Similarity	NPC51341
0.8271	Intermediate Similarity	NPC32152
0.8267	Intermediate Similarity	NPC183380
0.8255	Intermediate Similarity	NPC212142
0.8252	Intermediate Similarity	NPC475628
0.8243	Intermediate Similarity	NPC471608
0.8235	Intermediate Similarity	NPC261992
0.8222	Intermediate Similarity	NPC48623
0.8222	Intermediate Similarity	NPC168707
0.8219	Intermediate Similarity	NPC186033
0.8214	Intermediate Similarity	NPC196193
0.8209	Intermediate Similarity	NPC232295
0.8188	Intermediate Similarity	NPC325294
0.8188	Intermediate Similarity	NPC321822
0.8182	Intermediate Similarity	NPC279463
0.8176	Intermediate Similarity	NPC23807
0.8175	Intermediate Similarity	NPC61685
0.8162	Intermediate Similarity	NPC188997
0.8162	Intermediate Similarity	NPC204535
0.8162	Intermediate Similarity	NPC46586
0.8151	Intermediate Similarity	NPC5155
0.8148	Intermediate Similarity	NPC45663
0.8146	Intermediate Similarity	NPC195561
0.8146	Intermediate Similarity	NPC158784
0.8143	Intermediate Similarity	NPC97326
0.8134	Intermediate Similarity	NPC471449
0.8133	Intermediate Similarity	NPC95990
0.8129	Intermediate Similarity	NPC108164
0.8129	Intermediate Similarity	NPC186889
0.8125	Intermediate Similarity	NPC472800
0.812	Intermediate Similarity	NPC187993
0.812	Intermediate Similarity	NPC238176
0.8116	Intermediate Similarity	NPC133407
0.8116	Intermediate Similarity	NPC28476
0.8112	Intermediate Similarity	NPC71372
0.8108	Intermediate Similarity	NPC164183
0.8108	Intermediate Similarity	NPC253015
0.8108	Intermediate Similarity	NPC471065
0.8108	Intermediate Similarity	NPC133251
0.8102	Intermediate Similarity	NPC474130
0.8099	Intermediate Similarity	NPC51262
0.8095	Intermediate Similarity	NPC323126
0.8092	Intermediate Similarity	NPC2745
0.8092	Intermediate Similarity	NPC302915
0.8085	Intermediate Similarity	NPC249425
0.8082	Intermediate Similarity	NPC193920
0.8082	Intermediate Similarity	NPC221134
0.8079	Intermediate Similarity	NPC470208
0.8079	Intermediate Similarity	NPC295573
0.8058	Intermediate Similarity	NPC43000
0.8058	Intermediate Similarity	NPC100414
0.8054	Intermediate Similarity	NPC272619
0.8054	Intermediate Similarity	NPC286245
0.8045	Intermediate Similarity	NPC141001
0.8045	Intermediate Similarity	NPC69539
0.8039	Intermediate Similarity	NPC59692
0.8039	Intermediate Similarity	NPC157783
0.8039	Intermediate Similarity	NPC233467
0.8028	Intermediate Similarity	NPC472590
0.8028	Intermediate Similarity	NPC284232
0.8028	Intermediate Similarity	NPC258073
0.8025	Intermediate Similarity	NPC100936
0.8025	Intermediate Similarity	NPC1253
0.8014	Intermediate Similarity	NPC472151
0.8014	Intermediate Similarity	NPC472797
0.8014	Intermediate Similarity	NPC222108
0.8014	Intermediate Similarity	NPC96719
0.8014	Intermediate Similarity	NPC183781
0.8013	Intermediate Similarity	NPC179809
0.7987	Intermediate Similarity	NPC96447
0.7986	Intermediate Similarity	NPC252962
0.7986	Intermediate Similarity	NPC473107
0.7974	Intermediate Similarity	NPC259707
0.7972	Intermediate Similarity	NPC472798
0.7958	Intermediate Similarity	NPC475880
0.7947	Intermediate Similarity	NPC31325
0.7947	Intermediate Similarity	NPC224674
0.7947	Intermediate Similarity	NPC193473
0.7947	Intermediate Similarity	NPC15956
0.7947	Intermediate Similarity	NPC213074
0.7947	Intermediate Similarity	NPC275284
0.7947	Intermediate Similarity	NPC114505
0.7945	Intermediate Similarity	NPC134260
0.7941	Intermediate Similarity	NPC135467
0.7941	Intermediate Similarity	NPC260832
0.7933	Intermediate Similarity	NPC43508
0.7933	Intermediate Similarity	NPC271076
0.7933	Intermediate Similarity	NPC476301
0.7931	Intermediate Similarity	NPC79957
0.7931	Intermediate Similarity	NPC137580
0.7926	Intermediate Similarity	NPC283616
0.7926	Intermediate Similarity	NPC139047
0.7922	Intermediate Similarity	NPC48671
0.7922	Intermediate Similarity	NPC21902
0.7919	Intermediate Similarity	NPC472451
0.7917	Intermediate Similarity	NPC177712
0.7917	Intermediate Similarity	NPC24913
0.7917	Intermediate Similarity	NPC469610
0.7917	Intermediate Similarity	NPC77196
0.7914	Intermediate Similarity	NPC474237
0.7908	Intermediate Similarity	NPC214326
0.7908	Intermediate Similarity	NPC98624
0.7908	Intermediate Similarity	NPC185955
0.7908	Intermediate Similarity	NPC145979
0.7908	Intermediate Similarity	NPC469706
0.7908	Intermediate Similarity	NPC469707
0.7908	Intermediate Similarity	NPC182368
0.7908	Intermediate Similarity	NPC225815
0.7908	Intermediate Similarity	NPC9933
0.7908	Intermediate Similarity	NPC260781
0.7908	Intermediate Similarity	NPC218041
0.7905	Intermediate Similarity	NPC210192
0.7902	Intermediate Similarity	NPC474200
0.7902	Intermediate Similarity	NPC164804
0.7902	Intermediate Similarity	NPC211413
0.7902	Intermediate Similarity	NPC68205
0.7902	Intermediate Similarity	NPC118683
0.7902	Intermediate Similarity	NPC244888
0.7902	Intermediate Similarity	NPC293203
0.7899	Intermediate Similarity	NPC476332
0.7899	Intermediate Similarity	NPC473464
0.7899	Intermediate Similarity	NPC152946
0.7895	Intermediate Similarity	NPC291326
0.7895	Intermediate Similarity	NPC474856
0.7895	Intermediate Similarity	NPC290902
0.7895	Intermediate Similarity	NPC474940
0.7895	Intermediate Similarity	NPC474834
0.7895	Intermediate Similarity	NPC159697
0.7895	Intermediate Similarity	NPC117788
0.7895	Intermediate Similarity	NPC473876
0.7895	Intermediate Similarity	NPC474795
0.7895	Intermediate Similarity	NPC303013
0.7895	Intermediate Similarity	NPC130959
0.7887	Intermediate Similarity	NPC93962
0.7887	Intermediate Similarity	NPC472795
0.7887	Intermediate Similarity	NPC472796
0.7883	Intermediate Similarity	NPC473875
0.7883	Intermediate Similarity	NPC129176
0.7881	Intermediate Similarity	NPC102280
0.7881	Intermediate Similarity	NPC155564
0.7881	Intermediate Similarity	NPC248053
0.7877	Intermediate Similarity	NPC471522
0.7877	Intermediate Similarity	NPC92932
0.7875	Intermediate Similarity	NPC25889
0.7872	Intermediate Similarity	NPC473134
0.7871	Intermediate Similarity	NPC78809
0.7867	Intermediate Similarity	NPC129417
0.7867	Intermediate Similarity	NPC472155
0.7867	Intermediate Similarity	NPC217635
0.7867	Intermediate Similarity	NPC79429
0.7867	Intermediate Similarity	NPC225445
0.7867	Intermediate Similarity	NPC283995
0.7867	Intermediate Similarity	NPC471667
0.7867	Intermediate Similarity	NPC151704
0.7867	Intermediate Similarity	NPC470235
0.7862	Intermediate Similarity	NPC476617
0.7862	Intermediate Similarity	NPC476615
0.7862	Intermediate Similarity	NPC476616
0.7857	Intermediate Similarity	NPC76119
0.7857	Intermediate Similarity	NPC4286
0.7852	Intermediate Similarity	NPC476356
0.7852	Intermediate Similarity	NPC472353
0.7848	Intermediate Similarity	NPC185231
0.7847	Intermediate Similarity	NPC469611
0.7843	Intermediate Similarity	NPC181452

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 NPC473049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	889
0.2-0.3	1706
0.3-0.4	2773
0.4-0.5	1860
0.5-0.6	1076
0.6-0.7	432
0.7-0.8	42
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
0.8106	Intermediate Similarity	NPD6671	Approved
0.8085	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD6674	Discontinued
0.8	Intermediate Similarity	NPD2861	Phase 2
0.7914	Intermediate Similarity	NPD6696	Suspended
0.7832	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4908	Phase 1
0.7808	Intermediate Similarity	NPD7097	Phase 1
0.7793	Intermediate Similarity	NPD5735	Approved
0.7778	Intermediate Similarity	NPD7340	Approved
0.7724	Intermediate Similarity	NPD4140	Approved
0.7714	Intermediate Similarity	NPD5327	Phase 3
0.7639	Intermediate Similarity	NPD4625	Phase 3
0.7619	Intermediate Similarity	NPD6353	Approved
0.7603	Intermediate Similarity	NPD4060	Phase 1
0.7589	Intermediate Similarity	NPD4749	Approved
0.7556	Intermediate Similarity	NPD1398	Phase 1
0.7552	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3496	Discontinued
0.7484	Intermediate Similarity	NPD8455	Phase 2
0.7467	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD6100	Approved
0.7465	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1091	Approved
0.7447	Intermediate Similarity	NPD1610	Phase 2
0.7445	Intermediate Similarity	NPD7157	Approved
0.7434	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4624	Approved
0.7419	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5762	Approved
0.7417	Intermediate Similarity	NPD5763	Approved
0.7413	Intermediate Similarity	NPD8651	Approved
0.7397	Intermediate Similarity	NPD7095	Approved
0.7386	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3620	Phase 2
0.7365	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8312	Approved
0.7353	Intermediate Similarity	NPD8313	Approved
0.7342	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD7119	Phase 2
0.7324	Intermediate Similarity	NPD1611	Approved
0.7305	Intermediate Similarity	NPD7228	Approved
0.7293	Intermediate Similarity	NPD968	Approved
0.7286	Intermediate Similarity	NPD3091	Approved
0.7285	Intermediate Similarity	NPD4108	Discontinued
0.7267	Intermediate Similarity	NPD4097	Suspended
0.7261	Intermediate Similarity	NPD6273	Approved
0.7255	Intermediate Similarity	NPD7037	Approved
0.7248	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1613	Approved
0.7241	Intermediate Similarity	NPD3094	Phase 2
0.723	Intermediate Similarity	NPD7985	Registered
0.7226	Intermediate Similarity	NPD7635	Approved
0.7214	Intermediate Similarity	NPD7644	Approved
0.7212	Intermediate Similarity	NPD8127	Discontinued
0.7203	Intermediate Similarity	NPD3092	Approved
0.7197	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6584	Phase 3
0.7183	Intermediate Similarity	NPD1778	Approved
0.7183	Intermediate Similarity	NPD4626	Approved
0.7181	Intermediate Similarity	NPD8032	Phase 2
0.7161	Intermediate Similarity	NPD8166	Discontinued
0.7161	Intermediate Similarity	NPD7003	Approved
0.716	Intermediate Similarity	NPD5929	Approved
0.7159	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2232	Approved
0.7153	Intermediate Similarity	NPD2233	Approved
0.7153	Intermediate Similarity	NPD2230	Approved
0.7152	Intermediate Similarity	NPD6090	Discontinued
0.7143	Intermediate Similarity	NPD5736	Approved
0.7134	Intermediate Similarity	NPD7041	Phase 2
0.7134	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2238	Phase 2
0.7125	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5691	Approved
0.7113	Intermediate Similarity	NPD5585	Approved
0.7101	Intermediate Similarity	NPD7843	Approved
0.7095	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD7266	Discontinued
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7063	Intermediate Similarity	NPD3095	Discontinued
0.7063	Intermediate Similarity	NPD1653	Approved
0.7059	Intermediate Similarity	NPD2684	Approved
0.7045	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1548	Phase 1
0.7034	Intermediate Similarity	NPD2231	Phase 2
0.7034	Intermediate Similarity	NPD2235	Phase 2
0.7027	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7074	Phase 3
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.7	Intermediate Similarity	NPD7294	Phase 1
0.6994	Remote Similarity	NPD37	Approved
0.6993	Remote Similarity	NPD1357	Approved
0.6986	Remote Similarity	NPD6583	Phase 3
0.6986	Remote Similarity	NPD6582	Phase 2
0.6986	Remote Similarity	NPD3685	Discontinued
0.6981	Remote Similarity	NPD7447	Phase 1
0.6978	Remote Similarity	NPD5535	Approved
0.6978	Remote Similarity	NPD1138	Approved
0.6974	Remote Similarity	NPD6355	Discontinued
0.697	Remote Similarity	NPD4967	Phase 2
0.697	Remote Similarity	NPD4965	Approved
0.697	Remote Similarity	NPD4966	Approved
0.6966	Remote Similarity	NPD3705	Approved
0.6962	Remote Similarity	NPD5058	Phase 3
0.6959	Remote Similarity	NPD5844	Phase 1
0.6959	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7054	Approved
0.6954	Remote Similarity	NPD6663	Approved
0.695	Remote Similarity	NPD709	Approved
0.695	Remote Similarity	NPD6387	Discontinued
0.6944	Remote Similarity	NPD4059	Approved
0.6936	Remote Similarity	NPD7240	Approved
0.6933	Remote Similarity	NPD3027	Phase 3
0.6929	Remote Similarity	NPD5283	Phase 1
0.6928	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7831	Phase 2
0.6928	Remote Similarity	NPD7833	Phase 2
0.6923	Remote Similarity	NPD7741	Discontinued
0.6919	Remote Similarity	NPD7472	Approved
0.6913	Remote Similarity	NPD2237	Approved
0.6906	Remote Similarity	NPD1139	Approved
0.6906	Remote Similarity	NPD1137	Approved
0.6903	Remote Similarity	NPD2935	Discontinued
0.6894	Remote Similarity	NPD4727	Phase 1
0.6892	Remote Similarity	NPD2797	Approved
0.689	Remote Similarity	NPD5722	Discontinued
0.6887	Remote Similarity	NPD6798	Discontinued
0.6886	Remote Similarity	NPD6234	Discontinued
0.6883	Remote Similarity	NPD4536	Approved
0.6883	Remote Similarity	NPD4538	Approved
0.6883	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD27	Approved
0.6882	Remote Similarity	NPD2489	Approved
0.6871	Remote Similarity	NPD4359	Approved
0.6871	Remote Similarity	NPD7028	Phase 2
0.6865	Remote Similarity	NPD7698	Approved
0.6865	Remote Similarity	NPD7696	Phase 3
0.6865	Remote Similarity	NPD7697	Approved
0.6864	Remote Similarity	NPD3051	Approved
0.6861	Remote Similarity	NPD290	Approved
0.6859	Remote Similarity	NPD7030	Discontinued
0.6859	Remote Similarity	NPD2346	Discontinued
0.6857	Remote Similarity	NPD7313	Approved
0.6857	Remote Similarity	NPD7310	Approved
0.6857	Remote Similarity	NPD7311	Approved
0.6857	Remote Similarity	NPD7312	Approved
0.6855	Remote Similarity	NPD6666	Approved
0.6855	Remote Similarity	NPD6667	Approved
0.6842	Remote Similarity	NPD6233	Phase 2
0.6839	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD7251	Discontinued
0.6839	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4663	Approved
0.6835	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4628	Phase 3
0.6835	Remote Similarity	NPD4110	Phase 3
0.6828	Remote Similarity	NPD5846	Approved
0.6828	Remote Similarity	NPD6516	Phase 2
0.6828	Remote Similarity	NPD3019	Approved
0.6826	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2970	Approved
0.6824	Remote Similarity	NPD2969	Approved
0.6824	Remote Similarity	NPD1283	Approved
0.6818	Remote Similarity	NPD7309	Approved
0.6818	Remote Similarity	NPD2157	Approved
0.6818	Remote Similarity	NPD6653	Approved
0.6813	Remote Similarity	NPD7213	Phase 3
0.6813	Remote Similarity	NPD7212	Phase 2
0.6811	Remote Similarity	NPD6823	Phase 2
0.6807	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7199	Phase 2
0.6803	Remote Similarity	NPD1608	Approved
0.6802	Remote Similarity	NPD3751	Discontinued
0.68	Remote Similarity	NPD7808	Phase 3
0.68	Remote Similarity	NPD1712	Approved
0.6798	Remote Similarity	NPD7906	Approved
0.6797	Remote Similarity	NPD2979	Phase 3
0.6797	Remote Similarity	NPD3110	Approved
0.6797	Remote Similarity	NPD3109	Approved
0.6793	Remote Similarity	NPD6778	Approved
0.6793	Remote Similarity	NPD6779	Approved
0.6793	Remote Similarity	NPD6781	Approved
0.6793	Remote Similarity	NPD6782	Approved
0.6793	Remote Similarity	NPD6776	Approved
0.6793	Remote Similarity	NPD6777	Approved
0.6793	Remote Similarity	NPD6780	Approved
0.6792	Remote Similarity	NPD2677	Approved
0.6782	Remote Similarity	NPD6797	Phase 2
0.678	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4098	Discontinued
0.6776	Remote Similarity	NPD3268	Approved
0.6776	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7435	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