NPASS Compound

Structure

NPC469394 OpenBabel07101718242D 44 49 0 0 1 0 0 0 0 0999 V2000 4.8964 0.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6321 0.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4252 3.6430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3675 3.6430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0803 0.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2642 -4.7115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7124 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7124 -0.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7124 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7124 2.3558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8964 0.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4482 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2642 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2642 2.8269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8161 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2642 -2.8269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8964 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4482 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4482 0.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8964 -1.8846 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0803 -0.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2642 0.9423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4482 2.3558 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6321 1.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8161 0.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0803 -3.2981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0803 2.3558 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2642 -1.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8161 0.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8161 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8964 -2.8269 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8964 2.8269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0803 1.4135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0803 -1.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2642 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6321 2.8269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 2.8269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4482 -1.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7124 -3.2981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0803 -4.2404 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 18 1 0 0 0 0 2 19 2 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 6 43 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 21 1 0 0 0 0 10 34 1 0 0 0 0 11 35 1 0 0 0 0 12 20 2 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 27 2 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 29 1 0 0 0 0 16 26 1 0 0 0 0 16 31 2 0 0 0 0 17 28 2 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 37 1 0 0 0 0 21 33 1 0 0 0 0 21 36 1 1 0 0 0 22 36 1 6 0 0 0 23 35 1 1 0 0 0 24 38 1 1 0 0 0 25 32 2 0 0 0 0 25 39 1 0 0 0 0 26 32 1 0 0 0 0 26 40 2 0 0 0 0 27 32 1 0 0 0 0 27 44 1 0 0 0 0 28 33 1 0 0 0 0 28 43 1 0 0 0 0 29 34 1 0 0 0 0 29 35 1 1 0 0 0 30 36 1 0 0 0 0 30 41 2 0 0 0 0 31 44 1 0 0 0 0 33 42 1 0 0 0 0 35 5 1 1 0 0 0 36 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.29
Volume:	600.381
LogP:	5.458
LogD:	3.879
LogS:	-4.664
# Rotatable Bonds:	3
TPSA:	125.04
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	5.193
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.224
MDCK Permeability:	1.4483051018032711e-05
Pgp-inhibitor:	0.838
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.843
30% Bioavailability (F30%):	0.65

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	89.39832305908203%
Volume Distribution (VD):	0.75
Pgp-substrate:	5.919275283813477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.093
CYP1A2-substrate:	0.453
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.253
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.716
CYP2D6-inhibitor:	0.655
CYP2D6-substrate:	0.307
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	10.732
Half-life (T1/2):	0.046

ADMET: Toxicity

hERG Blockers:	0.525
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.207
Rat Oral Acute Toxicity:	0.674
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.58
Carcinogencity:	0.713
Eye Corrosion:	0.003
Eye Irritation:	0.427
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC469394

Natural Product ID:	NPC469394
*Common Name:**	Dichrostachine O
IUPAC Name:	2-[(4R,4aS,8aR)-4-[[(1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-8-hydroxy-7-methoxy-3-methyl-5-oxo-1,4,8,8a-tetrahydronaphthalen-4a-yl]-5,7-dihydroxychromen-4-one
Synonyms:	Dichrostachine O
Standard InCHIKey:	LVNKBVBEDBVHKZ-NINURHNOSA-N
Standard InCHI:	InChI=1S/C36H44O8/c1-18-8-9-21-33(42)28(43-6)17-30(41)36(21,31-16-26(40)32-25(39)12-20(37)13-27(32)44-31)22(18)14-23-19(2)24(38)15-29-34(3,4)10-7-11-35(23,29)5/h8,12-13,16-17,21-24,29,33,37-39,42H,2,7,9-11,14-15H2,1,3-6H3/t21-,22+,23-,24-,29-,33?,35+,36-/m0/s1
SMILES:	COC1=CC(=O)[C@@]2([C@H](C1O)CC=C([C@H]2C[C@H]1C(=C)[C@@H](O)C[C@@H]2[C@]1(C)CCCC2(C)C)C)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077627
PubChem CID:	44557417
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO15669	Dichrostachys cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19761234]
NPO15669	Dichrostachys cinerea	Species	Fabaceae	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
IC50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	25000.0	nM	PMID[571168]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	10.0	uM	PMID[571168]

☑ 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 NPC469394 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	438
0.1-0.2	1569
0.2-0.3	3121
0.3-0.4	7252
0.4-0.5	10146
0.5-0.6	6088
0.6-0.7	5682
0.7-0.8	5755
0.8-0.85	2476
0.85-0.9	156
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9568	High Similarity	NPC469393
0.9383	High Similarity	NPC286074
0.9383	High Similarity	NPC54903
0.9379	High Similarity	NPC85047
0.9379	High Similarity	NPC17274
0.9379	High Similarity	NPC120857
0.9375	High Similarity	NPC469395
0.9264	High Similarity	NPC20734
0.9207	High Similarity	NPC193698
0.913	High Similarity	NPC61382
0.913	High Similarity	NPC103816
0.9119	High Similarity	NPC164427
0.9096	High Similarity	NPC471969
0.9042	High Similarity	NPC294149
0.903	High Similarity	NPC188079
0.9018	High Similarity	NPC476295
0.897	High Similarity	NPC472622
0.8951	High Similarity	NPC472055
0.8938	High Similarity	NPC68727
0.8931	High Similarity	NPC470337
0.8931	High Similarity	NPC113608
0.8931	High Similarity	NPC268992
0.8931	High Similarity	NPC51824
0.8931	High Similarity	NPC470338
0.8922	High Similarity	NPC472620
0.8916	High Similarity	NPC102810
0.8909	High Similarity	NPC472621
0.8889	High Similarity	NPC472617
0.8889	High Similarity	NPC470339
0.8862	High Similarity	NPC315306
0.8862	High Similarity	NPC313717
0.8862	High Similarity	NPC251144
0.8862	High Similarity	NPC241387
0.8861	High Similarity	NPC307052
0.8861	High Similarity	NPC139966
0.8855	High Similarity	NPC478060
0.8855	High Similarity	NPC470374
0.8855	High Similarity	NPC471975
0.8855	High Similarity	NPC470377
0.8855	High Similarity	NPC478059
0.8834	High Similarity	NPC472618
0.8834	High Similarity	NPC297212
0.882	High Similarity	NPC175192
0.8812	High Similarity	NPC56232
0.8812	High Similarity	NPC244583
0.8812	High Similarity	NPC470340
0.8812	High Similarity	NPC180944
0.8812	High Similarity	NPC161881
0.8812	High Similarity	NPC150123
0.8812	High Similarity	NPC10807
0.881	High Similarity	NPC118128
0.8802	High Similarity	NPC472619
0.8797	High Similarity	NPC10097
0.8795	High Similarity	NPC178173
0.8788	High Similarity	NPC12461
0.8773	High Similarity	NPC197856
0.8773	High Similarity	NPC46736
0.8765	High Similarity	NPC192587
0.8765	High Similarity	NPC98943
0.8765	High Similarity	NPC478050
0.8758	High Similarity	NPC112701
0.8758	High Similarity	NPC326592
0.8758	High Similarity	NPC109594
0.8758	High Similarity	NPC155686
0.8758	High Similarity	NPC469405
0.8757	High Similarity	NPC475080
0.875	High Similarity	NPC328740
0.875	High Similarity	NPC207346
0.875	High Similarity	NPC209846
0.875	High Similarity	NPC289774
0.875	High Similarity	NPC473131
0.875	High Similarity	NPC470675
0.875	High Similarity	NPC477897
0.875	High Similarity	NPC46564
0.8743	High Similarity	NPC105414
0.8743	High Similarity	NPC324522
0.8743	High Similarity	NPC234497
0.8743	High Similarity	NPC470341
0.8743	High Similarity	NPC472058
0.8735	High Similarity	NPC469664
0.8727	High Similarity	NPC206605
0.8727	High Similarity	NPC472059
0.872	High Similarity	NPC195136
0.872	High Similarity	NPC101731
0.872	High Similarity	NPC470810
0.872	High Similarity	NPC476280
0.8712	High Similarity	NPC257166
0.8712	High Similarity	NPC183851
0.8712	High Similarity	NPC63454
0.8704	High Similarity	NPC470681
0.8704	High Similarity	NPC304745
0.8704	High Similarity	NPC111341
0.8698	High Similarity	NPC476159
0.869	High Similarity	NPC297195
0.869	High Similarity	NPC475212
0.869	High Similarity	NPC207574
0.869	High Similarity	NPC291795
0.8688	High Similarity	NPC225854
0.8683	High Similarity	NPC207575
0.8683	High Similarity	NPC13481
0.8683	High Similarity	NPC320741
0.8683	High Similarity	NPC476255
0.8683	High Similarity	NPC171985
0.8683	High Similarity	NPC251336
0.8675	High Similarity	NPC63438
0.8675	High Similarity	NPC472053
0.8675	High Similarity	NPC474240
0.8667	High Similarity	NPC305987
0.8667	High Similarity	NPC113163
0.8667	High Similarity	NPC97812
0.8667	High Similarity	NPC278427
0.8667	High Similarity	NPC288131
0.8667	High Similarity	NPC165970
0.8667	High Similarity	NPC142252
0.8667	High Similarity	NPC66618
0.8667	High Similarity	NPC87431
0.8667	High Similarity	NPC158188
0.8667	High Similarity	NPC26326
0.8667	High Similarity	NPC84324
0.8663	High Similarity	NPC244903
0.8659	High Similarity	NPC172202
0.8659	High Similarity	NPC51247
0.8659	High Similarity	NPC476410
0.8659	High Similarity	NPC15815
0.8659	High Similarity	NPC105584
0.8659	High Similarity	NPC117418
0.8659	High Similarity	NPC284127
0.8659	High Similarity	NPC90497
0.8659	High Similarity	NPC53545
0.8655	High Similarity	NPC469345
0.8655	High Similarity	NPC46958
0.865	High Similarity	NPC215917
0.865	High Similarity	NPC32867
0.865	High Similarity	NPC56049
0.865	High Similarity	NPC20530
0.865	High Similarity	NPC54830
0.865	High Similarity	NPC10754
0.865	High Similarity	NPC78492
0.865	High Similarity	NPC208152
0.8647	High Similarity	NPC213052
0.8642	High Similarity	NPC223701
0.8642	High Similarity	NPC7989
0.8642	High Similarity	NPC268193
0.8642	High Similarity	NPC472583
0.8634	High Similarity	NPC474021
0.8634	High Similarity	NPC178484
0.8634	High Similarity	NPC474023
0.8634	High Similarity	NPC46882
0.8634	High Similarity	NPC471677
0.8634	High Similarity	NPC132990
0.8631	High Similarity	NPC218226
0.8631	High Similarity	NPC243877
0.8631	High Similarity	NPC223413
0.8631	High Similarity	NPC470456
0.8631	High Similarity	NPC193222
0.8631	High Similarity	NPC474024
0.8631	High Similarity	NPC476306
0.8631	High Similarity	NPC260266
0.8625	High Similarity	NPC471114
0.8623	High Similarity	NPC472057
0.8623	High Similarity	NPC472049
0.8623	High Similarity	NPC475888
0.8623	High Similarity	NPC472051
0.8623	High Similarity	NPC314653
0.8623	High Similarity	NPC316262
0.8623	High Similarity	NPC294722
0.8616	High Similarity	NPC91902
0.8616	High Similarity	NPC470670
0.8616	High Similarity	NPC473133
0.8616	High Similarity	NPC85773
0.8616	High Similarity	NPC47388
0.8614	High Similarity	NPC211107
0.8614	High Similarity	NPC201800
0.8614	High Similarity	NPC474150
0.8614	High Similarity	NPC473012
0.8614	High Similarity	NPC474162
0.8613	High Similarity	NPC208069
0.8608	High Similarity	NPC224714
0.8606	High Similarity	NPC155302
0.8606	High Similarity	NPC475784
0.8606	High Similarity	NPC299436
0.8606	High Similarity	NPC472631
0.8606	High Similarity	NPC161947
0.8606	High Similarity	NPC321399
0.8606	High Similarity	NPC472630
0.8606	High Similarity	NPC476283
0.8605	High Similarity	NPC476199
0.8605	High Similarity	NPC476210
0.8598	High Similarity	NPC475184
0.8598	High Similarity	NPC271741
0.8598	High Similarity	NPC272196
0.8598	High Similarity	NPC287789
0.8598	High Similarity	NPC1796
0.8596	High Similarity	NPC86809
0.8596	High Similarity	NPC477992
0.8596	High Similarity	NPC477991
0.8596	High Similarity	NPC232412
0.8596	High Similarity	NPC475398
0.8596	High Similarity	NPC98667
0.8589	High Similarity	NPC217706

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 NPC469394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	915
0.2-0.3	1795
0.3-0.4	2626
0.4-0.5	1999
0.5-0.6	933
0.6-0.7	341
0.7-0.8	135
0.8-0.85	23
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8589	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD4380	Phase 2
0.8512	High Similarity	NPD6166	Phase 2
0.8512	High Similarity	NPD6167	Clinical (unspecified phase)
0.8512	High Similarity	NPD6168	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6959	Discontinued
0.8415	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7054	Approved
0.8354	Intermediate Similarity	NPD1934	Approved
0.8314	Intermediate Similarity	NPD7074	Phase 3
0.8314	Intermediate Similarity	NPD7472	Approved
0.8303	Intermediate Similarity	NPD2801	Approved
0.8276	Intermediate Similarity	NPD7808	Phase 3
0.8263	Intermediate Similarity	NPD7075	Discontinued
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7473	Discontinued
0.8218	Intermediate Similarity	NPD7251	Discontinued
0.8204	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD3818	Discontinued
0.8193	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD6797	Phase 2
0.8148	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6801	Discontinued
0.8086	Intermediate Similarity	NPD1511	Approved
0.8084	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD2800	Approved
0.8059	Intermediate Similarity	NPD5494	Approved
0.8057	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1549	Phase 2
0.7989	Intermediate Similarity	NPD8434	Phase 2
0.7988	Intermediate Similarity	NPD3882	Suspended
0.7988	Intermediate Similarity	NPD1512	Approved
0.7987	Intermediate Similarity	NPD2796	Approved
0.7977	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7411	Suspended
0.7943	Intermediate Similarity	NPD5844	Phase 1
0.7929	Intermediate Similarity	NPD5402	Approved
0.7925	Intermediate Similarity	NPD1510	Phase 2
0.7921	Intermediate Similarity	NPD8312	Approved
0.7921	Intermediate Similarity	NPD8313	Approved
0.7912	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6651	Approved
0.7901	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD8150	Discontinued
0.7888	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7875	Intermediate Similarity	NPD6100	Approved
0.7875	Intermediate Similarity	NPD6099	Approved
0.7831	Intermediate Similarity	NPD5403	Approved
0.7818	Intermediate Similarity	NPD2533	Approved
0.7818	Intermediate Similarity	NPD2532	Approved
0.7818	Intermediate Similarity	NPD2534	Approved
0.7809	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD4628	Phase 3
0.7791	Intermediate Similarity	NPD3750	Approved
0.7758	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD1607	Approved
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7683	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1240	Approved
0.7668	Intermediate Similarity	NPD8151	Discontinued
0.7661	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD7390	Discontinued
0.763	Intermediate Similarity	NPD3749	Approved
0.7602	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD6234	Discontinued
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD5760	Phase 2
0.7558	Intermediate Similarity	NPD5761	Phase 2
0.7557	Intermediate Similarity	NPD3787	Discontinued
0.7553	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3226	Approved
0.7529	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7485	Intermediate Similarity	NPD3748	Approved
0.7485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD6779	Approved
0.7435	Intermediate Similarity	NPD6780	Approved
0.7435	Intermediate Similarity	NPD6781	Approved
0.7435	Intermediate Similarity	NPD6782	Approved
0.7435	Intermediate Similarity	NPD6776	Approved
0.7435	Intermediate Similarity	NPD6777	Approved
0.7435	Intermediate Similarity	NPD6778	Approved
0.7411	Intermediate Similarity	NPD7783	Phase 2
0.7411	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7696	Phase 3
0.7409	Intermediate Similarity	NPD7435	Discontinued
0.7409	Intermediate Similarity	NPD7697	Approved
0.7409	Intermediate Similarity	NPD7698	Approved
0.7401	Intermediate Similarity	NPD7199	Phase 2
0.7371	Intermediate Similarity	NPD7871	Phase 2
0.7371	Intermediate Similarity	NPD7870	Phase 2
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8455	Phase 2
0.7354	Intermediate Similarity	NPD4360	Phase 2
0.7354	Intermediate Similarity	NPD4363	Phase 3
0.7347	Intermediate Similarity	NPD7701	Phase 2
0.7333	Intermediate Similarity	NPD1551	Phase 2
0.7329	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7801	Approved
0.7322	Intermediate Similarity	NPD7240	Approved
0.7318	Intermediate Similarity	NPD3926	Phase 2
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD920	Approved
0.7303	Intermediate Similarity	NPD1247	Approved
0.7294	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7263	Intermediate Similarity	NPD5710	Approved
0.7263	Intermediate Similarity	NPD5711	Approved
0.7254	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.7251	Intermediate Similarity	NPD6273	Approved
0.724	Intermediate Similarity	NPD7699	Phase 2
0.724	Intermediate Similarity	NPD7700	Phase 2
0.7239	Intermediate Similarity	NPD943	Approved
0.7239	Intermediate Similarity	NPD1613	Approved
0.7239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2935	Discontinued
0.7228	Intermediate Similarity	NPD7685	Pre-registration
0.7225	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7584	Approved
0.7202	Intermediate Similarity	NPD1243	Approved
0.7195	Intermediate Similarity	NPD230	Phase 1
0.7194	Intermediate Similarity	NPD8320	Phase 1
0.7194	Intermediate Similarity	NPD8319	Approved
0.7193	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD919	Approved
0.7188	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD2344	Approved
0.7182	Intermediate Similarity	NPD2403	Approved
0.7173	Intermediate Similarity	NPD6534	Approved
0.7173	Intermediate Similarity	NPD6535	Approved
0.717	Intermediate Similarity	NPD8651	Approved
0.7167	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD7003	Approved
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7907	Approved
0.7076	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3027	Phase 3
0.7047	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4361	Phase 2
0.7045	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8285	Discontinued
0.7018	Intermediate Similarity	NPD6190	Approved
0.7018	Intermediate Similarity	NPD2309	Approved
0.7012	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD7097	Phase 1
0.7006	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD4749	Approved
0.7	Intermediate Similarity	NPD6674	Discontinued
0.6995	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6832	Phase 2
0.699	Remote Similarity	NPD4111	Phase 1
0.699	Remote Similarity	NPD4665	Approved
0.6988	Remote Similarity	NPD6355	Discontinued
0.6988	Remote Similarity	NPD447	Suspended
0.6981	Remote Similarity	NPD1610	Phase 2
0.6977	Remote Similarity	NPD3300	Phase 2
0.6976	Remote Similarity	NPD8404	Phase 2
0.6975	Remote Similarity	NPD2798	Approved
0.6971	Remote Similarity	NPD1653	Approved
0.6963	Remote Similarity	NPD8361	Approved
0.6963	Remote Similarity	NPD8360	Approved
0.6952	Remote Similarity	NPD8368	Discontinued
0.6943	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6212	Phase 3
0.6943	Remote Similarity	NPD6213	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