NPASS Compound

Structure

CID113550 OpenBabel06191715462D 30 35 0 0 1 0 0 0 0 0999 V2000 -2.6492 0.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6856 -0.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5969 5.5183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3929 -0.0025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4710 3.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9056 2.7488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6608 0.9975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7948 2.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6315 4.6993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8633 4.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6883 1.0516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9081 2.8200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7948 1.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0314 4.5476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5269 1.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4660 3.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6608 2.9975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3477 1.9918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0289 4.4764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5269 2.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8994 0.4371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0712 0.9975 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5944 5.4471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3929 0.9975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4564 3.7147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8687 3.9756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7493 5.1700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2700 3.1666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3483 1.9583 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 11 1 0 0 0 0 2 21 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 16 2 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 25 1 0 0 0 0 9 27 1 0 0 0 0 10 26 1 0 0 0 0 10 28 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 6 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 12 1 1 0 0 0 18 29 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 6 0 0 0 21 30 1 0 0 0 0 22 13 1 6 0 0 0 22 29 1 0 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.13
Volume:	392.232
LogP:	3.977
LogD:	3.592
LogS:	-6.1
# Rotatable Bonds:	4
TPSA:	77.14
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	4.32
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.813
MDCK Permeability:	5.8412937505636364e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	87.99678802490234%
Volume Distribution (VD):	0.952
Pgp-substrate:	6.135263442993164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.313
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.888
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.973
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	15.351
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.614
Drug-inuced Liver Injury (DILI):	0.747
AMES Toxicity:	0.431
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.861
Skin Sensitization:	0.88
Carcinogencity:	0.976
Eye Corrosion:	0.003
Eye Irritation:	0.329
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC113550

Natural Product ID:	NPC113550
*Common Name:**	Beilschmin D
IUPAC Name:	4-methoxy-6-[(1S,3S,4R,5S)-1-(7-methoxy-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-3-yl]-1,3-benzodioxole
Synonyms:	Beilschmin D
Standard InCHIKey:	CVGWCATWCAZNFN-YMIXRQRSSA-N
Standard InCHI:	InChI=1S/C22H22O8/c1-11-18(12-5-14(23-3)19-16(6-12)25-9-27-19)29-22(21(11,2)30-22)13-7-15(24-4)20-17(8-13)26-10-28-20/h5-8,11,18H,9-10H2,1-4H3/t11-,18+,21+,22+/m1/s1
SMILES:	COc1cc(cc2c1OCO2)[C@H]1O[C@@]2([C@]([C@@H]1C)(O2)C)c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204390
PubChem CID:	71455792
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[10479343]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11277756]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724849]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[16724849]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27214307]
NPO2861	Pentaceraster regulus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28981263]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722494]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5844	Schlumbergera truncata	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3331	Hedysarum sachalinense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5582	Inocybe aeruginascens	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6053	Veronica intercedens	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1462	Amomum sulcatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9215	Papaver glaucum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO772	Bosistoa floydii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27884	Sphacelaria arctica	Species	Sphacelariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4888	Salvia divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2861	Pentaceraster regulus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO345	Quercus laurifolia	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5844	Schlumbergera truncata	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6791	Malva rotundifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6305	Euphorbia jaxartica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO134	Cassia artemisioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7401	Centaurea dealbata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO569	Micromelum integerrimum	Species	Rutaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[483101]

☑ 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 NPC113550 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	525
0.1-0.2	1591
0.2-0.3	4444
0.3-0.4	11315
0.4-0.5	7666
0.5-0.6	6527
0.6-0.7	8174
0.7-0.8	1958
0.8-0.85	371
0.85-0.9	101
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC121651
0.9771	High Similarity	NPC25333
0.9771	High Similarity	NPC49235
0.9771	High Similarity	NPC148893
0.9695	High Similarity	NPC31530
0.9621	High Similarity	NPC189474
0.9618	High Similarity	NPC1474
0.9542	High Similarity	NPC72046
0.9542	High Similarity	NPC65183
0.9542	High Similarity	NPC261812
0.9481	High Similarity	NPC46591
0.947	High Similarity	NPC266848
0.947	High Similarity	NPC136750
0.9412	High Similarity	NPC312199
0.9338	High Similarity	NPC56091
0.9318	High Similarity	NPC227160
0.9318	High Similarity	NPC192255
0.9318	High Similarity	NPC82111
0.9275	High Similarity	NPC185071
0.9275	High Similarity	NPC12728
0.9259	High Similarity	NPC11453
0.9242	High Similarity	NPC271208
0.9242	High Similarity	NPC233224
0.9237	High Similarity	NPC54321
0.9237	High Similarity	NPC328682
0.9237	High Similarity	NPC281864
0.9209	High Similarity	NPC141569
0.9209	High Similarity	NPC477701
0.9209	High Similarity	NPC166884
0.9203	High Similarity	NPC474295
0.9191	High Similarity	NPC283949
0.9185	High Similarity	NPC150534
0.916	High Similarity	NPC473093
0.916	High Similarity	NPC8050
0.916	High Similarity	NPC473092
0.9137	High Similarity	NPC298317
0.9137	High Similarity	NPC255566
0.9104	High Similarity	NPC7744
0.9104	High Similarity	NPC158526
0.9104	High Similarity	NPC171928
0.9104	High Similarity	NPC33611
0.9104	High Similarity	NPC16830
0.9104	High Similarity	NPC129687
0.9104	High Similarity	NPC100223
0.9091	High Similarity	NPC82862
0.9091	High Similarity	NPC57119
0.9091	High Similarity	NPC158471
0.9091	High Similarity	NPC165128
0.9091	High Similarity	NPC222127
0.9091	High Similarity	NPC226862
0.9065	High Similarity	NPC287124
0.9065	High Similarity	NPC311057
0.9058	High Similarity	NPC216434
0.9058	High Similarity	NPC226547
0.9058	High Similarity	NPC103448
0.9058	High Similarity	NPC177868
0.9051	High Similarity	NPC185908
0.9044	High Similarity	NPC474139
0.9007	High Similarity	NPC205316
0.8978	High Similarity	NPC143895
0.8971	High Similarity	NPC47181
0.8939	High Similarity	NPC186845
0.8939	High Similarity	NPC9891
0.8939	High Similarity	NPC88297
0.8939	High Similarity	NPC285725
0.8939	High Similarity	NPC50683
0.8939	High Similarity	NPC112571
0.8936	High Similarity	NPC92693
0.8936	High Similarity	NPC218841
0.8929	High Similarity	NPC472562
0.8929	High Similarity	NPC174522
0.8929	High Similarity	NPC80326
0.8913	High Similarity	NPC101807
0.8905	High Similarity	NPC18576
0.8905	High Similarity	NPC236522
0.8897	High Similarity	NPC196937
0.8873	High Similarity	NPC477702
0.8872	High Similarity	NPC158737
0.8857	High Similarity	NPC300798
0.8857	High Similarity	NPC58137
0.8849	High Similarity	NPC88640
0.8849	High Similarity	NPC123526
0.8849	High Similarity	NPC193666
0.8841	High Similarity	NPC32189
0.8811	High Similarity	NPC193779
0.8811	High Similarity	NPC212890
0.8803	High Similarity	NPC177644
0.8803	High Similarity	NPC191158
0.8794	High Similarity	NPC151423
0.8794	High Similarity	NPC40237
0.8788	High Similarity	NPC34902
0.8788	High Similarity	NPC18449
0.8788	High Similarity	NPC121783
0.8777	High Similarity	NPC474039
0.8777	High Similarity	NPC469981
0.8768	High Similarity	NPC34103
0.8768	High Similarity	NPC24490
0.8768	High Similarity	NPC165155
0.8768	High Similarity	NPC141765
0.8741	High Similarity	NPC475868
0.8741	High Similarity	NPC180953
0.8732	High Similarity	NPC474808
0.8732	High Similarity	NPC76415
0.8732	High Similarity	NPC218510
0.8723	High Similarity	NPC471908
0.8714	High Similarity	NPC9068
0.8696	High Similarity	NPC170779
0.8696	High Similarity	NPC256776
0.8696	High Similarity	NPC90083
0.8696	High Similarity	NPC185680
0.8696	High Similarity	NPC145722
0.869	High Similarity	NPC248132
0.869	High Similarity	NPC130449
0.8686	High Similarity	NPC147616
0.8686	High Similarity	NPC219671
0.8686	High Similarity	NPC259742
0.8686	High Similarity	NPC104077
0.8676	High Similarity	NPC237169
0.8676	High Similarity	NPC470624
0.8671	High Similarity	NPC472713
0.8671	High Similarity	NPC187774
0.8671	High Similarity	NPC172171
0.8671	High Similarity	NPC473046
0.8671	High Similarity	NPC118385
0.8671	High Similarity	NPC475000
0.8671	High Similarity	NPC239254
0.8671	High Similarity	NPC326144
0.8671	High Similarity	NPC472712
0.8662	High Similarity	NPC210354
0.8662	High Similarity	NPC176586
0.8643	High Similarity	NPC196420
0.8639	High Similarity	NPC164082
0.8633	High Similarity	NPC174191
0.8633	High Similarity	NPC126409
0.8633	High Similarity	NPC135777
0.8633	High Similarity	NPC99572
0.8633	High Similarity	NPC142547
0.863	High Similarity	NPC35877
0.863	High Similarity	NPC55158
0.863	High Similarity	NPC85141
0.863	High Similarity	NPC286235
0.863	High Similarity	NPC51328
0.863	High Similarity	NPC95392
0.863	High Similarity	NPC55715
0.863	High Similarity	NPC240521
0.8611	High Similarity	NPC318286
0.8611	High Similarity	NPC327651
0.8603	High Similarity	NPC476748
0.8601	High Similarity	NPC324962
0.8601	High Similarity	NPC474288
0.8601	High Similarity	NPC265154
0.8582	High Similarity	NPC53722
0.8582	High Similarity	NPC156376
0.8582	High Similarity	NPC201404
0.8582	High Similarity	NPC290714
0.8571	High Similarity	NPC473989
0.8571	High Similarity	NPC78047
0.8571	High Similarity	NPC25695
0.8571	High Similarity	NPC197166
0.8571	High Similarity	NPC172818
0.8562	High Similarity	NPC71726
0.8561	High Similarity	NPC312713
0.8561	High Similarity	NPC244983
0.8561	High Similarity	NPC172676
0.8561	High Similarity	NPC216929
0.8561	High Similarity	NPC326095
0.8561	High Similarity	NPC65933
0.8561	High Similarity	NPC301641
0.8561	High Similarity	NPC126935
0.8561	High Similarity	NPC80241
0.8561	High Similarity	NPC57268
0.8552	High Similarity	NPC162193
0.8552	High Similarity	NPC252286
0.8552	High Similarity	NPC154971
0.8552	High Similarity	NPC321696
0.8552	High Similarity	NPC321958
0.8551	High Similarity	NPC204215
0.8551	High Similarity	NPC475856
0.8551	High Similarity	NPC175067
0.8542	High Similarity	NPC179521
0.8542	High Similarity	NPC50696
0.8542	High Similarity	NPC84181
0.854	High Similarity	NPC134764
0.854	High Similarity	NPC63574
0.854	High Similarity	NPC171550
0.8531	High Similarity	NPC229172
0.8531	High Similarity	NPC230538
0.8531	High Similarity	NPC103637
0.8531	High Similarity	NPC246947
0.8531	High Similarity	NPC472714
0.8531	High Similarity	NPC5262
0.8531	High Similarity	NPC36531
0.8514	High Similarity	NPC210642
0.8514	High Similarity	NPC13985
0.8514	High Similarity	NPC303519
0.8511	High Similarity	NPC166184
0.8503	High Similarity	NPC262455
0.8503	High Similarity	NPC177476
0.8503	High Similarity	NPC477698
0.8493	Intermediate Similarity	NPC39657

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 NPC113550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	871
0.2-0.3	2039
0.3-0.4	2913
0.4-0.5	1578
0.5-0.6	956
0.6-0.7	360
0.7-0.8	32
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD3705	Approved
0.8235	Intermediate Similarity	NPD4966	Approved
0.8235	Intermediate Similarity	NPD4965	Approved
0.8235	Intermediate Similarity	NPD4967	Phase 2
0.8129	Intermediate Similarity	NPD6234	Discontinued
0.8071	Intermediate Similarity	NPD3027	Phase 3
0.8039	Intermediate Similarity	NPD37	Approved
0.7879	Intermediate Similarity	NPD5283	Phase 1
0.7826	Intermediate Similarity	NPD2981	Phase 2
0.7778	Intermediate Similarity	NPD7228	Approved
0.777	Intermediate Similarity	NPD2982	Phase 2
0.777	Intermediate Similarity	NPD2983	Phase 2
0.7712	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.7676	Intermediate Similarity	NPD3018	Phase 2
0.7593	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7240	Approved
0.7534	Intermediate Similarity	NPD1613	Approved
0.7534	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1357	Approved
0.7403	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6674	Discontinued
0.7267	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4908	Phase 1
0.7246	Intermediate Similarity	NPD3818	Discontinued
0.7237	Intermediate Similarity	NPD1375	Discontinued
0.7226	Intermediate Similarity	NPD7124	Phase 2
0.7215	Intermediate Similarity	NPD1653	Approved
0.7195	Intermediate Similarity	NPD5494	Approved
0.7171	Intermediate Similarity	NPD3539	Phase 1
0.7162	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6111	Discontinued
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3382	Approved
0.7143	Intermediate Similarity	NPD3383	Approved
0.7143	Intermediate Similarity	NPD3384	Approved
0.7133	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD7266	Discontinued
0.7124	Intermediate Similarity	NPD3540	Phase 1
0.7115	Intermediate Similarity	NPD5058	Phase 3
0.7089	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD7074	Phase 3
0.7034	Intermediate Similarity	NPD4749	Approved
0.7021	Intermediate Similarity	NPD5536	Phase 2
0.702	Intermediate Similarity	NPD3657	Discovery
0.7014	Intermediate Similarity	NPD1091	Approved
0.7011	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD4210	Discontinued
0.6995	Remote Similarity	NPD7680	Approved
0.6981	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7685	Pre-registration
0.6961	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7472	Approved
0.6957	Remote Similarity	NPD4005	Discontinued
0.6954	Remote Similarity	NPD3620	Phase 2
0.6954	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3817	Phase 2
0.6933	Remote Similarity	NPD5109	Approved
0.6933	Remote Similarity	NPD1934	Approved
0.6933	Remote Similarity	NPD5110	Phase 2
0.6933	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5111	Phase 2
0.6923	Remote Similarity	NPD4237	Approved
0.6923	Remote Similarity	NPD4236	Phase 3
0.6914	Remote Similarity	NPD7028	Phase 2
0.6909	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2977	Approved
0.689	Remote Similarity	NPD2978	Approved
0.6883	Remote Similarity	NPD4108	Discontinued
0.6879	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7157	Approved
0.6879	Remote Similarity	NPD7466	Approved
0.6879	Remote Similarity	NPD4110	Phase 3
0.6867	Remote Similarity	NPD4625	Phase 3
0.6853	Remote Similarity	NPD1548	Phase 1
0.6839	Remote Similarity	NPD2438	Suspended
0.6839	Remote Similarity	NPD7808	Phase 3
0.6835	Remote Similarity	NPD228	Approved
0.6821	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6797	Phase 2
0.681	Remote Similarity	NPD4675	Approved
0.681	Remote Similarity	NPD4678	Approved
0.6807	Remote Similarity	NPD3882	Suspended
0.6806	Remote Similarity	NPD5585	Approved
0.6805	Remote Similarity	NPD3787	Discontinued
0.6803	Remote Similarity	NPD5327	Phase 3
0.68	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7843	Approved
0.6782	Remote Similarity	NPD7251	Discontinued
0.6782	Remote Similarity	NPD6559	Discontinued
0.6774	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6331	Phase 2
0.6766	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3926	Phase 2
0.6765	Remote Similarity	NPD5242	Approved
0.6759	Remote Similarity	NPD5126	Approved
0.6759	Remote Similarity	NPD5125	Phase 3
0.675	Remote Similarity	NPD4357	Discontinued
0.6748	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5353	Approved
0.6743	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2684	Approved
0.6732	Remote Similarity	NPD4060	Phase 1
0.6732	Remote Similarity	NPD2238	Phase 2
0.6731	Remote Similarity	NPD3454	Phase 3
0.6731	Remote Similarity	NPD2161	Phase 2
0.6725	Remote Similarity	NPD6166	Phase 2
0.6725	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7296	Approved
0.671	Remote Similarity	NPD6896	Approved
0.671	Remote Similarity	NPD6895	Approved
0.671	Remote Similarity	NPD7097	Phase 1
0.6709	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6232	Discontinued
0.6705	Remote Similarity	NPD5844	Phase 1
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved
0.6689	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6355	Discontinued
0.6688	Remote Similarity	NPD5735	Approved
0.6687	Remote Similarity	NPD2801	Approved
0.6686	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5005	Approved
0.6667	Remote Similarity	NPD5006	Approved
0.6667	Remote Similarity	NPD5588	Approved
0.6667	Remote Similarity	NPD4055	Discovery
0.6667	Remote Similarity	NPD3892	Phase 2
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6843	Phase 3
0.6648	Remote Similarity	NPD6842	Approved
0.6648	Remote Similarity	NPD6841	Approved
0.6648	Remote Similarity	NPD7549	Discontinued
0.6646	Remote Similarity	NPD5297	Approved
0.6645	Remote Similarity	NPD7095	Approved
0.6644	Remote Similarity	NPD17	Approved
0.6627	Remote Similarity	NPD919	Approved
0.6626	Remote Similarity	NPD5976	Discontinued
0.6625	Remote Similarity	NPD2219	Phase 1
0.6624	Remote Similarity	NPD2796	Approved
0.6623	Remote Similarity	NPD2979	Phase 3
0.6604	Remote Similarity	NPD5177	Phase 3
0.6604	Remote Similarity	NPD3060	Approved
0.6603	Remote Similarity	NPD4538	Approved
0.6603	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4536	Approved
0.6587	Remote Similarity	NPD8455	Phase 2
0.6582	Remote Similarity	NPD5762	Approved
0.6582	Remote Similarity	NPD5763	Approved
0.6581	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5124	Phase 1
0.6577	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4359	Approved
0.6575	Remote Similarity	NPD5691	Approved
0.6571	Remote Similarity	NPD5451	Approved
0.6564	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5960	Phase 3
0.6552	Remote Similarity	NPD3751	Discontinued
0.655	Remote Similarity	NPD1247	Approved
0.655	Remote Similarity	NPD8127	Discontinued
0.6547	Remote Similarity	NPD1358	Approved
0.6541	Remote Similarity	NPD4420	Approved
0.6538	Remote Similarity	NPD2492	Phase 1
0.6538	Remote Similarity	NPD6353	Approved
0.6533	Remote Similarity	NPD8651	Approved
0.6533	Remote Similarity	NPD2922	Phase 1
0.6528	Remote Similarity	NPD6387	Discontinued
0.6527	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6190	Approved
0.6519	Remote Similarity	NPD6099	Approved
0.6519	Remote Similarity	NPD6100	Approved
0.6516	Remote Similarity	NPD1558	Phase 1
0.6516	Remote Similarity	NPD4140	Approved
0.6514	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7229	Phase 3
0.651	Remote Similarity	NPD1840	Phase 2
0.651	Remote Similarity	NPD1608	Approved
0.6507	Remote Similarity	NPD1182	Approved
0.6506	Remote Similarity	NPD4380	Phase 2
0.6503	Remote Similarity	NPD4123	Phase 3
0.65	Remote Similarity	NPD1652	Phase 2
0.65	Remote Similarity	NPD4162	Approved
0.6494	Remote Similarity	NPD5718	Phase 2

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