NPASS Compound

Structure

NPC470937 OpenBabel07101719522D 33 37 0 0 1 0 0 0 0 0999 V2000 3.5497 -2.0959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9844 0.2789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4213 2.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2037 3.8391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7692 -2.1737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8636 -1.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9448 -2.5407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1335 -0.7457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2147 -2.0103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6938 -0.8244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9584 0.0943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2243 -1.5545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4888 -0.6358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4213 1.1813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6398 -0.1724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3887 1.9114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3091 -1.1128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0609 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1218 -1.4602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4213 0.2789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3887 1.0090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6398 1.6325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8583 0.2789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5304 2.1903 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8583 1.1813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5304 0.7301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2516 3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6522 -2.1903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2029 -0.1724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6398 2.5350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5304 2.1903 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 1 29 1 0 0 0 0 2 30 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 23 2 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 18 26 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 26 1 1 0 0 0 22 25 2 0 0 0 0 22 31 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 27 1 6 0 0 0 24 28 1 0 0 0 0 25 27 1 0 0 0 0 26 27 1 1 0 0 0 26 33 1 0 0 0 0 27 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.19
Volume:	461.779
LogP:	4.214
LogD:	3.712
LogS:	-5.438
# Rotatable Bonds:	6
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	3.868
Fsp3:	0.333
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:	-5.274
MDCK Permeability:	6.106828368501738e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.665
Plasma Protein Binding (PPB):	91.17694854736328%
Volume Distribution (VD):	0.724
Pgp-substrate:	5.167567253112793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.833
CYP2C19-substrate:	0.875
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.845
CYP2D6-inhibitor:	0.225
CYP2D6-substrate:	0.937
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	9.909
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.876
Human Hepatotoxicity (H-HT):	0.591
Drug-inuced Liver Injury (DILI):	0.367
AMES Toxicity:	0.459
Rat Oral Acute Toxicity:	0.819
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.076
Carcinogencity:	0.7
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC470937

Natural Product ID:	NPC470937
*Common Name:**	8B-O-Methylrocaglaol
IUPAC Name:	(1R,3S,3aR,8bS)-6,8,8b-trimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-ol
Synonyms:	8B-O-Methylrocaglaol
Standard InCHIKey:	OLHDAACFTXKKEU-CYUUXAIJSA-N
Standard InCHI:	InChI=1S/C27H28O6/c1-29-19-12-10-18(11-13-19)26-21(17-8-6-5-7-9-17)16-24(28)27(26,32-4)25-22(31-3)14-20(30-2)15-23(25)33-26/h5-15,21,24,28H,16H2,1-4H3/t21-,24+,26-,27+/m0/s1
SMILES:	COc1ccc(cc1)[C@]12Oc3c([C@]2(OC)[C@@H](C[C@H]1c1ccccc1)O)c(OC)cc(c3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2331822
PubChem CID:	21670100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0003109] Flavaglines

*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
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO4720	Aglaia perviridis	Species	Meliaceae	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
ED50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[491763]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[491763]

☑ 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 NPC470937 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	435
0.1-0.2	1337
0.2-0.3	3596
0.3-0.4	9673
0.4-0.5	9507
0.5-0.6	5359
0.6-0.7	9387
0.7-0.8	2983
0.8-0.85	386
0.85-0.9	27
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC184607
0.95	High Similarity	NPC20360
0.9306	High Similarity	NPC51543
0.9241	High Similarity	NPC87363
0.9116	High Similarity	NPC164152
0.9054	High Similarity	NPC189730
0.8933	High Similarity	NPC209473
0.8874	High Similarity	NPC310399
0.8874	High Similarity	NPC73422
0.8857	High Similarity	NPC474687
0.8832	High Similarity	NPC162801
0.8808	High Similarity	NPC329743
0.8794	High Similarity	NPC475836
0.8786	High Similarity	NPC3049
0.8777	High Similarity	NPC124085
0.8777	High Similarity	NPC117048
0.8705	High Similarity	NPC85435
0.8693	High Similarity	NPC90336
0.8652	High Similarity	NPC18189
0.8652	High Similarity	NPC262585
0.8652	High Similarity	NPC20829
0.8633	High Similarity	NPC13005
0.863	High Similarity	NPC211758
0.863	High Similarity	NPC87794
0.863	High Similarity	NPC317053
0.863	High Similarity	NPC324492
0.8613	High Similarity	NPC39064
0.8613	High Similarity	NPC87224
0.8613	High Similarity	NPC222572
0.8613	High Similarity	NPC47283
0.8593	High Similarity	NPC294156
0.8593	High Similarity	NPC256015
0.859	High Similarity	NPC475621
0.8571	High Similarity	NPC328567
0.8571	High Similarity	NPC470936
0.8571	High Similarity	NPC327412
0.8571	High Similarity	NPC320671
0.8571	High Similarity	NPC320970
0.8562	High Similarity	NPC181615
0.8561	High Similarity	NPC12875
0.8561	High Similarity	NPC17343
0.8561	High Similarity	NPC280653
0.8561	High Similarity	NPC207892
0.8561	High Similarity	NPC300875
0.8561	High Similarity	NPC103799
0.8561	High Similarity	NPC150011
0.8561	High Similarity	NPC118114
0.8561	High Similarity	NPC196765
0.8561	High Similarity	NPC268917
0.8561	High Similarity	NPC206224
0.8561	High Similarity	NPC228369
0.8561	High Similarity	NPC164574
0.8561	High Similarity	NPC129106
0.8561	High Similarity	NPC129784
0.8561	High Similarity	NPC476166
0.8561	High Similarity	NPC236014
0.8552	High Similarity	NPC274721
0.8552	High Similarity	NPC135767
0.8552	High Similarity	NPC155392
0.8542	High Similarity	NPC108674
0.8542	High Similarity	NPC476334
0.8511	High Similarity	NPC223008
0.8511	High Similarity	NPC225696
0.8511	High Similarity	NPC198154
0.8511	High Similarity	NPC296915
0.8511	High Similarity	NPC97834
0.8511	High Similarity	NPC115335
0.8503	High Similarity	NPC260397
0.8493	Intermediate Similarity	NPC277951
0.8493	Intermediate Similarity	NPC470097
0.8493	Intermediate Similarity	NPC114119
0.8493	Intermediate Similarity	NPC317237
0.8493	Intermediate Similarity	NPC471415
0.8493	Intermediate Similarity	NPC44530
0.8489	Intermediate Similarity	NPC27187
0.8489	Intermediate Similarity	NPC470225
0.8472	Intermediate Similarity	NPC184797
0.8472	Intermediate Similarity	NPC309124
0.8467	Intermediate Similarity	NPC471215
0.8467	Intermediate Similarity	NPC283049
0.8467	Intermediate Similarity	NPC26879
0.8467	Intermediate Similarity	NPC262573
0.8467	Intermediate Similarity	NPC50315
0.8467	Intermediate Similarity	NPC230479
0.8462	Intermediate Similarity	NPC477938
0.844	Intermediate Similarity	NPC263064
0.844	Intermediate Similarity	NPC92805
0.844	Intermediate Similarity	NPC215037
0.8429	Intermediate Similarity	NPC181497
0.8429	Intermediate Similarity	NPC271945
0.8414	Intermediate Similarity	NPC100482
0.8414	Intermediate Similarity	NPC87725
0.8414	Intermediate Similarity	NPC178054
0.8414	Intermediate Similarity	NPC277331
0.8414	Intermediate Similarity	NPC263261
0.8403	Intermediate Similarity	NPC236306
0.8403	Intermediate Similarity	NPC232164
0.8403	Intermediate Similarity	NPC473739
0.8394	Intermediate Similarity	NPC278552
0.8394	Intermediate Similarity	NPC207179
0.8394	Intermediate Similarity	NPC167571
0.8392	Intermediate Similarity	NPC327735
0.8392	Intermediate Similarity	NPC126101
0.8392	Intermediate Similarity	NPC141717
0.8382	Intermediate Similarity	NPC474160
0.8375	Intermediate Similarity	NPC271755
0.8375	Intermediate Similarity	NPC254071
0.8375	Intermediate Similarity	NPC149502
0.8375	Intermediate Similarity	NPC222665
0.8367	Intermediate Similarity	NPC475492
0.8356	Intermediate Similarity	NPC472353
0.8356	Intermediate Similarity	NPC107161
0.8345	Intermediate Similarity	NPC213607
0.8345	Intermediate Similarity	NPC38664
0.8345	Intermediate Similarity	NPC174787
0.8345	Intermediate Similarity	NPC254759
0.8345	Intermediate Similarity	NPC291101
0.8345	Intermediate Similarity	NPC27495
0.8345	Intermediate Similarity	NPC266197
0.8345	Intermediate Similarity	NPC160283
0.8345	Intermediate Similarity	NPC182509
0.8345	Intermediate Similarity	NPC274717
0.8345	Intermediate Similarity	NPC53986
0.8344	Intermediate Similarity	NPC321972
0.8344	Intermediate Similarity	NPC324517
0.8344	Intermediate Similarity	NPC329343
0.8322	Intermediate Similarity	NPC11727
0.8322	Intermediate Similarity	NPC151224
0.8322	Intermediate Similarity	NPC61946
0.8322	Intermediate Similarity	NPC125579
0.8322	Intermediate Similarity	NPC15109
0.8322	Intermediate Similarity	NPC164787
0.8299	Intermediate Similarity	NPC163508
0.8299	Intermediate Similarity	NPC173203
0.8299	Intermediate Similarity	NPC477616
0.8298	Intermediate Similarity	NPC293203
0.8298	Intermediate Similarity	NPC68205
0.8298	Intermediate Similarity	NPC211413
0.8298	Intermediate Similarity	NPC164804
0.8298	Intermediate Similarity	NPC244888
0.8298	Intermediate Similarity	NPC472590
0.8298	Intermediate Similarity	NPC118683
0.8288	Intermediate Similarity	NPC471389
0.8288	Intermediate Similarity	NPC247291
0.8288	Intermediate Similarity	NPC5155
0.8288	Intermediate Similarity	NPC311530
0.8286	Intermediate Similarity	NPC93962
0.8276	Intermediate Similarity	NPC292882
0.8276	Intermediate Similarity	NPC22517
0.8276	Intermediate Similarity	NPC471388
0.8272	Intermediate Similarity	NPC107739
0.8267	Intermediate Similarity	NPC227516
0.8267	Intermediate Similarity	NPC20757
0.8267	Intermediate Similarity	NPC329836
0.8264	Intermediate Similarity	NPC227503
0.8264	Intermediate Similarity	NPC230734
0.8264	Intermediate Similarity	NPC302701
0.8264	Intermediate Similarity	NPC306441
0.8264	Intermediate Similarity	NPC78047
0.8264	Intermediate Similarity	NPC162659
0.8264	Intermediate Similarity	NPC265433
0.8264	Intermediate Similarity	NPC270456
0.8264	Intermediate Similarity	NPC269091
0.8264	Intermediate Similarity	NPC474639
0.8264	Intermediate Similarity	NPC16435
0.8264	Intermediate Similarity	NPC248727
0.8261	Intermediate Similarity	NPC81641
0.8252	Intermediate Similarity	NPC474478
0.8252	Intermediate Similarity	NPC476616
0.8252	Intermediate Similarity	NPC16485
0.8252	Intermediate Similarity	NPC287745
0.8252	Intermediate Similarity	NPC476617
0.8252	Intermediate Similarity	NPC476615
0.8248	Intermediate Similarity	NPC38761
0.8248	Intermediate Similarity	NPC76465
0.8243	Intermediate Similarity	NPC280092
0.8243	Intermediate Similarity	NPC15659
0.8243	Intermediate Similarity	NPC93323
0.8243	Intermediate Similarity	NPC304894
0.8243	Intermediate Similarity	NPC45257
0.8243	Intermediate Similarity	NPC12641
0.8239	Intermediate Similarity	NPC230219
0.8227	Intermediate Similarity	NPC474491
0.8221	Intermediate Similarity	NPC23593
0.8219	Intermediate Similarity	NPC22317
0.8212	Intermediate Similarity	NPC470826
0.8212	Intermediate Similarity	NPC470098
0.8212	Intermediate Similarity	NPC473266
0.8207	Intermediate Similarity	NPC94994
0.8201	Intermediate Similarity	NPC276212
0.82	Intermediate Similarity	NPC101376
0.82	Intermediate Similarity	NPC16269
0.82	Intermediate Similarity	NPC21776
0.8194	Intermediate Similarity	NPC94750
0.8194	Intermediate Similarity	NPC121812
0.8194	Intermediate Similarity	NPC126409
0.8194	Intermediate Similarity	NPC260898
0.8194	Intermediate Similarity	NPC112939
0.8194	Intermediate Similarity	NPC93783
0.8194	Intermediate Similarity	NPC47398

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 NPC470937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	805
0.2-0.3	1761
0.3-0.4	2738
0.4-0.5	1840
0.5-0.6	1064
0.6-0.7	525
0.7-0.8	76
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD4908	Phase 1
0.8357	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1610	Phase 2
0.8056	Intermediate Similarity	NPD5735	Approved
0.8014	Intermediate Similarity	NPD2861	Phase 2
0.7987	Intermediate Similarity	NPD7199	Phase 2
0.7902	Intermediate Similarity	NPD3027	Phase 3
0.7832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1548	Phase 1
0.7785	Intermediate Similarity	NPD5762	Approved
0.7785	Intermediate Similarity	NPD5763	Approved
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6002	Phase 3
0.7667	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6005	Phase 3
0.7667	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6004	Phase 3
0.7635	Intermediate Similarity	NPD6353	Approved
0.7632	Intermediate Similarity	NPD3892	Phase 2
0.7632	Intermediate Similarity	NPD7466	Approved
0.7606	Intermediate Similarity	NPD4749	Approved
0.7603	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6355	Discontinued
0.7566	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8651	Approved
0.7534	Intermediate Similarity	NPD4625	Phase 3
0.7533	Intermediate Similarity	NPD5588	Approved
0.7532	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD3094	Phase 2
0.7483	Intermediate Similarity	NPD5327	Phase 3
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4536	Approved
0.7467	Intermediate Similarity	NPD4538	Approved
0.7465	Intermediate Similarity	NPD1091	Approved
0.7464	Intermediate Similarity	NPD7157	Approved
0.7463	Intermediate Similarity	NPD2684	Approved
0.7451	Intermediate Similarity	NPD1652	Phase 2
0.745	Intermediate Similarity	NPD5124	Phase 1
0.745	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6516	Phase 2
0.7447	Intermediate Similarity	NPD5846	Approved
0.7407	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD4965	Approved
0.7407	Intermediate Similarity	NPD4967	Phase 2
0.74	Intermediate Similarity	NPD6653	Approved
0.7388	Intermediate Similarity	NPD290	Approved
0.7383	Intermediate Similarity	NPD3620	Phase 2
0.7383	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7843	Approved
0.7372	Intermediate Similarity	NPD7213	Phase 3
0.7372	Intermediate Similarity	NPD7212	Phase 2
0.7329	Intermediate Similarity	NPD4624	Approved
0.7329	Intermediate Similarity	NPD37	Approved
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7447	Phase 1
0.7317	Intermediate Similarity	NPD6234	Discontinued
0.7315	Intermediate Similarity	NPD6233	Phase 2
0.7303	Intermediate Similarity	NPD7033	Discontinued
0.7303	Intermediate Similarity	NPD5960	Phase 3
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6674	Discontinued
0.7222	Intermediate Similarity	NPD3092	Approved
0.7222	Intermediate Similarity	NPD1934	Approved
0.7211	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4380	Phase 2
0.7202	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6166	Phase 2
0.7202	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7183	Intermediate Similarity	NPD7741	Discontinued
0.7181	Intermediate Similarity	NPD7095	Approved
0.7178	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8455	Phase 2
0.7162	Intermediate Similarity	NPD3018	Phase 2
0.7152	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD6362	Approved
0.7124	Intermediate Similarity	NPD7097	Phase 1
0.7118	Intermediate Similarity	NPD7228	Approved
0.7107	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD422	Phase 1
0.7097	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5844	Phase 1
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.7071	Intermediate Similarity	NPD5283	Phase 1
0.707	Intermediate Similarity	NPD4628	Phase 3
0.7066	Intermediate Similarity	NPD5494	Approved
0.7059	Intermediate Similarity	NPD2157	Approved
0.7055	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6559	Discontinued
0.7051	Intermediate Similarity	NPD1549	Phase 2
0.7048	Intermediate Similarity	NPD7075	Discontinued
0.7044	Intermediate Similarity	NPD6799	Approved
0.7039	Intermediate Similarity	NPD2238	Phase 2
0.7032	Intermediate Similarity	NPD6099	Approved
0.7032	Intermediate Similarity	NPD6100	Approved
0.7025	Intermediate Similarity	NPD2677	Approved
0.7018	Intermediate Similarity	NPD3818	Discontinued
0.7012	Intermediate Similarity	NPD6801	Discontinued
0.7007	Intermediate Similarity	NPD2982	Phase 2
0.7007	Intermediate Similarity	NPD6583	Phase 3
0.7007	Intermediate Similarity	NPD6582	Phase 2
0.7007	Intermediate Similarity	NPD2983	Phase 2
0.7	Intermediate Similarity	NPD5535	Approved
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6599	Discontinued
0.6988	Remote Similarity	NPD3882	Suspended
0.6988	Remote Similarity	NPD7768	Phase 2
0.6982	Remote Similarity	NPD3787	Discontinued
0.698	Remote Similarity	NPD5647	Approved
0.698	Remote Similarity	NPD6584	Phase 3
0.6975	Remote Similarity	NPD1653	Approved
0.6972	Remote Similarity	NPD6671	Approved
0.697	Remote Similarity	NPD2801	Approved
0.6966	Remote Similarity	NPD5125	Phase 3
0.6966	Remote Similarity	NPD3095	Discontinued
0.6966	Remote Similarity	NPD5126	Approved
0.6962	Remote Similarity	NPD4535	Phase 3
0.6962	Remote Similarity	NPD3750	Approved
0.6957	Remote Similarity	NPD6273	Approved
0.6954	Remote Similarity	NPD7240	Approved
0.6951	Remote Similarity	NPD6072	Discontinued
0.6951	Remote Similarity	NPD7411	Suspended
0.6946	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3091	Approved
0.6939	Remote Similarity	NPD2981	Phase 2
0.6928	Remote Similarity	NPD3817	Phase 2
0.6928	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8127	Discontinued
0.6914	Remote Similarity	NPD7549	Discontinued
0.6914	Remote Similarity	NPD5403	Approved
0.6913	Remote Similarity	NPD2797	Approved
0.6906	Remote Similarity	NPD5451	Approved
0.6899	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5401	Approved
0.6892	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3657	Discovery
0.6879	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3122	Phase 3
0.6871	Remote Similarity	NPD3705	Approved
0.6867	Remote Similarity	NPD7819	Suspended
0.6863	Remote Similarity	NPD3163	Approved
0.6863	Remote Similarity	NPD3162	Approved
0.6859	Remote Similarity	NPD3748	Approved
0.6859	Remote Similarity	NPD1510	Phase 2
0.6857	Remote Similarity	NPD7685	Pre-registration
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6331	Phase 2
0.6852	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6696	Suspended
0.6845	Remote Similarity	NPD3749	Approved
0.6839	Remote Similarity	NPD7074	Phase 3
0.6835	Remote Similarity	NPD5958	Discontinued
0.6832	Remote Similarity	NPD1511	Approved
0.6832	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6581	Approved
0.6828	Remote Similarity	NPD6580	Approved
0.6826	Remote Similarity	NPD5402	Approved
0.6824	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD968	Approved
0.68	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3268	Approved
0.6795	Remote Similarity	NPD2200	Suspended
0.679	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7019	Approved
0.679	Remote Similarity	NPD7020	Approved
0.6784	Remote Similarity	NPD3051	Approved
0.6782	Remote Similarity	NPD7054	Approved
0.6781	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3685	Discontinued
0.6774	Remote Similarity	NPD4340	Discontinued
0.677	Remote Similarity	NPD6667	Approved
0.677	Remote Similarity	NPD6666	Approved
0.677	Remote Similarity	NPD6815	Approved
0.6765	Remote Similarity	NPD940	Approved
0.6765	Remote Similarity	NPD846	Approved
0.6755	Remote Similarity	NPD3690	Phase 2
0.6755	Remote Similarity	NPD3691	Phase 2
0.6753	Remote Similarity	NPD7477	Discontinued
0.6753	Remote Similarity	NPD4062	Phase 3
0.6753	Remote Similarity	NPD7265	Discontinued
0.675	Remote Similarity	NPD4110	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data