NPASS Compound

Structure

NPC470642 OpenBabel07101718222D 38 44 0 0 1 0 0 0 0 0999 V2000 -3.8005 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5428 -5.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0428 -6.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1775 -4.3141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0540 -6.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2219 -4.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3209 -5.5799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -7.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3394 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 -6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8005 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 -2.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -0.0827 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 -1.4103 -7.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8116 -6.2518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7516 -2.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7516 -1.2737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 1 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 34 1 0 0 0 0 13 35 1 0 0 0 0 13 36 1 0 0 0 0 14 37 1 0 0 0 0 14 38 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 18 12 1 1 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 35 1 0 0 0 0 20 36 1 0 0 0 0 21 26 2 0 0 0 0 21 37 1 0 0 0 0 22 15 1 6 0 0 0 22 24 1 0 0 0 0 23 27 2 0 0 0 0 24 28 1 6 0 0 0 25 23 1 1 0 0 0 25 29 1 0 0 0 0 26 27 1 0 0 0 0 26 38 1 0 0 0 0 27 33 1 0 0 0 0 28 30 2 3 0 0 0 28 31 1 0 0 0 0 29 32 2 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	521.2
Volume:	510.472
LogP:	4.391
LogD:	3.629
LogS:	-4.132
# Rotatable Bonds:	5
TPSA:	101.55
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	4.152
Fsp3:	0.517
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	2.079650221276097e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	97.58234405517578%
Volume Distribution (VD):	1.472
Pgp-substrate:	1.8239333629608154%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.875
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.693

ADMET: Excretion

Clearance (CL):	11.644
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.041
Carcinogencity:	0.401
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.832

Download Data

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

Natural Product: NPC470642

Natural Product ID:	NPC470642
*Common Name:**	(3As,4R,5R,10Bs)-5-(1,3-Benzodioxol-5-Yl)-N-Cycloheptyl-10-Methoxy-1-Oxo-3A,4,5,10B-Tetrahydro-3H-[2]Benzofuro[5,4-F][1,3]Benzodioxole-4-Carboxamide
IUPAC Name:	(3aS,4R,5R,10bS)-5-(1,3-benzodioxol-5-yl)-N-cycloheptyl-10-methoxy-1-oxo-3a,4,5,10b-tetrahydro-3H-[2]benzofuro[5,4-f][1,3]benzodioxole-4-carboxamide
Synonyms:
Standard InCHIKey:	GSDVCWPJFFHRKK-MLHDVUGYSA-N
Standard InCHI:	InChI=1S/C29H31NO8/c1-33-27-23-17(11-21-26(27)38-14-37-21)22(15-8-9-19-20(10-15)36-13-35-19)24(18-12-34-29(32)25(18)23)28(31)30-16-6-4-2-3-5-7-16/h8-11,16,18,22,24-25H,2-7,12-14H2,1H3,(H,30,31)/t18-,22+,24-,25-/m0/s1
SMILES:	COc1c2[C@H]3C(=O)OC[C@H]3[C@@H]([C@@H](c2cc2c1OCO2)c1ccc2c(c1)OCO2)C(=NC1CCCCCC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2147051
PubChem CID:	71451062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO7890	Cleistanthus indochinensis	Species	Phyllanthaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22938151]
NPO7890	Cleistanthus indochinensis	Species	Phyllanthaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	26.0	ug.mL-1	PMID[524878]

☑ 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 NPC470642 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	257
0.1-0.2	1145
0.2-0.3	3136
0.3-0.4	8962
0.4-0.5	10074
0.5-0.6	6284
0.6-0.7	11635
0.7-0.8	1174
0.8-0.85	28
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8713	High Similarity	NPC96593
0.8663	High Similarity	NPC288149
0.8529	High Similarity	NPC273578
0.8497	Intermediate Similarity	NPC470637
0.8488	Intermediate Similarity	NPC207584
0.8488	Intermediate Similarity	NPC19947
0.8486	Intermediate Similarity	NPC470646
0.843	Intermediate Similarity	NPC237946
0.843	Intermediate Similarity	NPC32373
0.8402	Intermediate Similarity	NPC149505
0.8382	Intermediate Similarity	NPC181168
0.8382	Intermediate Similarity	NPC115281
0.8382	Intermediate Similarity	NPC163527
0.8353	Intermediate Similarity	NPC210642
0.8353	Intermediate Similarity	NPC13985
0.8343	Intermediate Similarity	NPC262455
0.8343	Intermediate Similarity	NPC177476
0.8286	Intermediate Similarity	NPC268718
0.8286	Intermediate Similarity	NPC150943
0.8286	Intermediate Similarity	NPC91634
0.8286	Intermediate Similarity	NPC119910
0.8256	Intermediate Similarity	NPC245948
0.8239	Intermediate Similarity	NPC100465
0.8239	Intermediate Similarity	NPC152424
0.8225	Intermediate Similarity	NPC101755
0.8225	Intermediate Similarity	NPC304687
0.8225	Intermediate Similarity	NPC104024
0.8225	Intermediate Similarity	NPC80230
0.8225	Intermediate Similarity	NPC65574
0.8208	Intermediate Similarity	NPC103197
0.8208	Intermediate Similarity	NPC30009
0.8202	Intermediate Similarity	NPC222531
0.8162	Intermediate Similarity	NPC474009
0.8156	Intermediate Similarity	NPC474042
0.8156	Intermediate Similarity	NPC174734
0.8146	Intermediate Similarity	NPC116759
0.8146	Intermediate Similarity	NPC14294
0.8142	Intermediate Similarity	NPC196771
0.814	Intermediate Similarity	NPC164082
0.8136	Intermediate Similarity	NPC115624
0.8079	Intermediate Similarity	NPC474770
0.8066	Intermediate Similarity	NPC117911
0.8056	Intermediate Similarity	NPC306475
0.8047	Intermediate Similarity	NPC191158
0.8047	Intermediate Similarity	NPC92693
0.8047	Intermediate Similarity	NPC177644
0.8047	Intermediate Similarity	NPC218841
0.8035	Intermediate Similarity	NPC303519
0.8034	Intermediate Similarity	NPC209411
0.8034	Intermediate Similarity	NPC239890
0.8023	Intermediate Similarity	NPC474043
0.8023	Intermediate Similarity	NPC477698
0.8011	Intermediate Similarity	NPC185498
0.8011	Intermediate Similarity	NPC79322
0.8011	Intermediate Similarity	NPC18306
0.8	Intermediate Similarity	NPC475768
0.7989	Intermediate Similarity	NPC56184
0.7989	Intermediate Similarity	NPC198796
0.7989	Intermediate Similarity	NPC22130
0.7989	Intermediate Similarity	NPC116838
0.7977	Intermediate Similarity	NPC24425
0.7966	Intermediate Similarity	NPC19600
0.7953	Intermediate Similarity	NPC193779
0.7953	Intermediate Similarity	NPC87295
0.7943	Intermediate Similarity	NPC178574
0.7943	Intermediate Similarity	NPC65591
0.7935	Intermediate Similarity	NPC184624
0.7933	Intermediate Similarity	NPC191352
0.7933	Intermediate Similarity	NPC258322
0.7931	Intermediate Similarity	NPC474975
0.7929	Intermediate Similarity	NPC210354
0.7929	Intermediate Similarity	NPC176586
0.7929	Intermediate Similarity	NPC151423
0.7929	Intermediate Similarity	NPC40237
0.7923	Intermediate Similarity	NPC179240
0.7923	Intermediate Similarity	NPC477883
0.7921	Intermediate Similarity	NPC125713
0.7919	Intermediate Similarity	NPC477695
0.7919	Intermediate Similarity	NPC474965
0.7919	Intermediate Similarity	NPC174512
0.7919	Intermediate Similarity	NPC145569
0.7919	Intermediate Similarity	NPC293757
0.7919	Intermediate Similarity	NPC668
0.7919	Intermediate Similarity	NPC216223
0.791	Intermediate Similarity	NPC239113
0.791	Intermediate Similarity	NPC473900
0.791	Intermediate Similarity	NPC115123
0.7898	Intermediate Similarity	NPC348849
0.7898	Intermediate Similarity	NPC178195
0.7892	Intermediate Similarity	NPC107739
0.7886	Intermediate Similarity	NPC477699
0.7886	Intermediate Similarity	NPC104353
0.7882	Intermediate Similarity	NPC474288
0.7872	Intermediate Similarity	NPC474661
0.7872	Intermediate Similarity	NPC475919
0.787	Intermediate Similarity	NPC246474
0.787	Intermediate Similarity	NPC162851
0.787	Intermediate Similarity	NPC218092
0.7869	Intermediate Similarity	NPC474051
0.7861	Intermediate Similarity	NPC262804
0.7861	Intermediate Similarity	NPC40654
0.7861	Intermediate Similarity	NPC304821
0.7857	Intermediate Similarity	NPC83049
0.7857	Intermediate Similarity	NPC320471
0.7857	Intermediate Similarity	NPC118162
0.7853	Intermediate Similarity	NPC234730
0.7849	Intermediate Similarity	NPC23593
0.7849	Intermediate Similarity	NPC263955
0.7849	Intermediate Similarity	NPC3982
0.7845	Intermediate Similarity	NPC475865
0.7838	Intermediate Similarity	NPC477881
0.7836	Intermediate Similarity	NPC475000
0.7836	Intermediate Similarity	NPC166884
0.7836	Intermediate Similarity	NPC141569
0.7836	Intermediate Similarity	NPC477701
0.7833	Intermediate Similarity	NPC15212
0.7829	Intermediate Similarity	NPC477700
0.7821	Intermediate Similarity	NPC325122
0.7817	Intermediate Similarity	NPC80472
0.7814	Intermediate Similarity	NPC471180
0.7814	Intermediate Similarity	NPC311912
0.7809	Intermediate Similarity	NPC301897
0.7809	Intermediate Similarity	NPC477380
0.7807	Intermediate Similarity	NPC35266
0.7807	Intermediate Similarity	NPC29587
0.7802	Intermediate Similarity	NPC477884
0.7797	Intermediate Similarity	NPC136757
0.779	Intermediate Similarity	NPC61141
0.7784	Intermediate Similarity	NPC292712
0.7784	Intermediate Similarity	NPC474075
0.7784	Intermediate Similarity	NPC178737
0.7784	Intermediate Similarity	NPC471920
0.7784	Intermediate Similarity	NPC129930
0.7784	Intermediate Similarity	NPC471922
0.7784	Intermediate Similarity	NPC471921
0.7784	Intermediate Similarity	NPC20114
0.7784	Intermediate Similarity	NPC114550
0.7784	Intermediate Similarity	NPC312006
0.7778	Intermediate Similarity	NPC78944
0.7772	Intermediate Similarity	NPC88557
0.7771	Intermediate Similarity	NPC473989
0.7766	Intermediate Similarity	NPC169605
0.7766	Intermediate Similarity	NPC236089
0.7765	Intermediate Similarity	NPC477885
0.7765	Intermediate Similarity	NPC474990
0.7753	Intermediate Similarity	NPC238834
0.7753	Intermediate Similarity	NPC186316
0.7746	Intermediate Similarity	NPC33832
0.7742	Intermediate Similarity	NPC474568
0.774	Intermediate Similarity	NPC474514
0.7735	Intermediate Similarity	NPC319749
0.7733	Intermediate Similarity	NPC143092
0.7733	Intermediate Similarity	NPC18211
0.773	Intermediate Similarity	NPC91043
0.7727	Intermediate Similarity	NPC32079
0.7719	Intermediate Similarity	NPC287124
0.7713	Intermediate Similarity	NPC477880
0.7713	Intermediate Similarity	NPC477882
0.7709	Intermediate Similarity	NPC109765
0.7701	Intermediate Similarity	NPC475794
0.7697	Intermediate Similarity	NPC198461
0.7697	Intermediate Similarity	NPC54179
0.7697	Intermediate Similarity	NPC312763
0.7692	Intermediate Similarity	NPC76687
0.7692	Intermediate Similarity	NPC196420
0.7692	Intermediate Similarity	NPC280778
0.7688	Intermediate Similarity	NPC474158
0.7688	Intermediate Similarity	NPC258128
0.7688	Intermediate Similarity	NPC471181
0.768	Intermediate Similarity	NPC239818
0.768	Intermediate Similarity	NPC189782
0.768	Intermediate Similarity	NPC218471
0.7667	Intermediate Similarity	NPC202495
0.7663	Intermediate Similarity	NPC471923
0.766	Intermediate Similarity	NPC474607
0.766	Intermediate Similarity	NPC473713
0.7657	Intermediate Similarity	NPC316676
0.7657	Intermediate Similarity	NPC325720
0.7654	Intermediate Similarity	NPC42871
0.7654	Intermediate Similarity	NPC188962
0.7654	Intermediate Similarity	NPC254163
0.7654	Intermediate Similarity	NPC202249
0.7647	Intermediate Similarity	NPC329816
0.7644	Intermediate Similarity	NPC167045
0.7644	Intermediate Similarity	NPC321696
0.7644	Intermediate Similarity	NPC321958
0.7644	Intermediate Similarity	NPC114120
0.764	Intermediate Similarity	NPC474606
0.7633	Intermediate Similarity	NPC11453
0.7627	Intermediate Similarity	NPC475756
0.7626	Intermediate Similarity	NPC235698
0.7624	Intermediate Similarity	NPC68619
0.7624	Intermediate Similarity	NPC241600
0.7624	Intermediate Similarity	NPC173726
0.7622	Intermediate Similarity	NPC475453
0.7622	Intermediate Similarity	NPC473531
0.7622	Intermediate Similarity	NPC167231
0.7622	Intermediate Similarity	NPC215802
0.7619	Intermediate Similarity	NPC474650
0.7616	Intermediate Similarity	NPC474295

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 NPC470642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	595
0.2-0.3	1235
0.3-0.4	2529
0.4-0.5	2593
0.5-0.6	1390
0.6-0.7	577
0.7-0.8	49
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.843	Intermediate Similarity	NPD4966	Approved
0.843	Intermediate Similarity	NPD4965	Approved
0.843	Intermediate Similarity	NPD4967	Phase 2
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8256	Intermediate Similarity	NPD37	Approved
0.8197	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD7199	Phase 2
0.8063	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7228	Approved
0.785	Intermediate Similarity	NPD7827	Phase 1
0.7838	Intermediate Similarity	NPD7240	Approved
0.768	Intermediate Similarity	NPD6746	Phase 2
0.7667	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD8151	Discontinued
0.7596	Intermediate Similarity	NPD6232	Discontinued
0.7586	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5005	Approved
0.7576	Intermediate Similarity	NPD5006	Approved
0.7568	Intermediate Similarity	NPD7473	Discontinued
0.7557	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD4420	Approved
0.7409	Intermediate Similarity	NPD6842	Approved
0.7409	Intermediate Similarity	NPD6843	Phase 3
0.7409	Intermediate Similarity	NPD6841	Approved
0.7405	Intermediate Similarity	NPD7315	Approved
0.7403	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7389	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7296	Approved
0.7377	Intermediate Similarity	NPD4055	Discovery
0.7374	Intermediate Similarity	NPD4005	Discontinued
0.7366	Intermediate Similarity	NPD5242	Approved
0.7366	Intermediate Similarity	NPD7801	Approved
0.7363	Intermediate Similarity	NPD7680	Approved
0.734	Intermediate Similarity	NPD3818	Discontinued
0.7317	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7874	Approved
0.7293	Intermediate Similarity	NPD6385	Approved
0.7293	Intermediate Similarity	NPD5090	Approved
0.7293	Intermediate Similarity	NPD6386	Approved
0.7293	Intermediate Similarity	NPD5089	Approved
0.7236	Intermediate Similarity	NPD2973	Approved
0.7236	Intermediate Similarity	NPD2974	Approved
0.7236	Intermediate Similarity	NPD2975	Approved
0.7228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7214	Intermediate Similarity	NPD4580	Approved
0.7175	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6778	Approved
0.7129	Intermediate Similarity	NPD6776	Approved
0.7129	Intermediate Similarity	NPD6780	Approved
0.7129	Intermediate Similarity	NPD6782	Approved
0.7129	Intermediate Similarity	NPD6781	Approved
0.7129	Intermediate Similarity	NPD6777	Approved
0.7129	Intermediate Similarity	NPD6779	Approved
0.7128	Intermediate Similarity	NPD5711	Approved
0.7128	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD4108	Discontinued
0.7122	Intermediate Similarity	NPD7999	Approved
0.712	Intermediate Similarity	NPD7819	Suspended
0.7115	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7783	Phase 2
0.7112	Intermediate Similarity	NPD5494	Approved
0.7111	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7930	Approved
0.7094	Intermediate Similarity	NPD2494	Approved
0.7094	Intermediate Similarity	NPD2493	Approved
0.7083	Intermediate Similarity	NPD7074	Phase 3
0.7073	Intermediate Similarity	NPD4583	Approved
0.7073	Intermediate Similarity	NPD4582	Approved
0.7062	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2532	Approved
0.7056	Intermediate Similarity	NPD2534	Approved
0.7056	Intermediate Similarity	NPD2533	Approved
0.7031	Intermediate Similarity	NPD7054	Approved
0.7027	Intermediate Similarity	NPD1465	Phase 2
0.7026	Intermediate Similarity	NPD2971	Approved
0.7026	Intermediate Similarity	NPD2968	Approved
0.7024	Intermediate Similarity	NPD7698	Approved
0.7024	Intermediate Similarity	NPD7697	Approved
0.7024	Intermediate Similarity	NPD4004	Approved
0.7024	Intermediate Similarity	NPD4002	Approved
0.7024	Intermediate Similarity	NPD7696	Phase 3
0.7022	Intermediate Similarity	NPD6331	Phase 2
0.701	Intermediate Similarity	NPD3452	Approved
0.701	Intermediate Similarity	NPD3450	Approved
0.7005	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD4357	Discontinued
0.6995	Remote Similarity	NPD7472	Approved
0.699	Remote Similarity	NPD8320	Phase 1
0.699	Remote Similarity	NPD7870	Phase 2
0.699	Remote Similarity	NPD8319	Approved
0.699	Remote Similarity	NPD7871	Phase 2
0.6989	Remote Similarity	NPD4477	Approved
0.6989	Remote Similarity	NPD5353	Approved
0.6989	Remote Similarity	NPD4476	Approved
0.6985	Remote Similarity	NPD2490	Approved
0.6985	Remote Similarity	NPD2488	Approved
0.6978	Remote Similarity	NPD7427	Discontinued
0.6977	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7549	Discontinued
0.6974	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD1934	Approved
0.6971	Remote Similarity	NPD7701	Phase 2
0.6968	Remote Similarity	NPD6723	Discontinued
0.6963	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4481	Phase 3
0.6961	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6502	Phase 2
0.6952	Remote Similarity	NPD3882	Suspended
0.6942	Remote Similarity	NPD7435	Discontinued
0.6939	Remote Similarity	NPD7280	Phase 3
0.6939	Remote Similarity	NPD7281	Phase 3
0.6935	Remote Similarity	NPD2801	Approved
0.6935	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7972	Discontinued
0.6935	Remote Similarity	NPD7861	Discontinued
0.6935	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4110	Phase 3
0.6927	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6559	Discontinued
0.6914	Remote Similarity	NPD2157	Approved
0.6895	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8059	Phase 3
0.6895	Remote Similarity	NPD8127	Discontinued
0.6891	Remote Similarity	NPD7177	Discontinued
0.6888	Remote Similarity	NPD7808	Phase 3
0.6881	Remote Similarity	NPD6535	Approved
0.6881	Remote Similarity	NPD6534	Approved
0.6875	Remote Similarity	NPD6166	Phase 2
0.6875	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6797	Phase 2
0.6868	Remote Similarity	NPD4739	Approved
0.6868	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4675	Approved
0.6865	Remote Similarity	NPD4678	Approved
0.686	Remote Similarity	NPD7497	Discontinued
0.6859	Remote Similarity	NPD3051	Approved
0.6859	Remote Similarity	NPD3787	Discontinued
0.6854	Remote Similarity	NPD1375	Discontinued
0.6849	Remote Similarity	NPD8491	Approved
0.6845	Remote Similarity	NPD8455	Phase 2
0.6837	Remote Similarity	NPD7685	Pre-registration
0.6837	Remote Similarity	NPD7251	Discontinued
0.6837	Remote Similarity	NPD7038	Approved
0.6837	Remote Similarity	NPD7039	Approved
0.6835	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD8150	Discontinued
0.6833	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7565	Approved
0.6825	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8366	Approved
0.6818	Remote Similarity	NPD8407	Phase 2
0.6816	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6625	Approved
0.6811	Remote Similarity	NPD7458	Discontinued
0.6804	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2161	Phase 2
0.6798	Remote Similarity	NPD2438	Suspended
0.6796	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8404	Phase 2
0.6791	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7007	Discovery
0.678	Remote Similarity	NPD7700	Phase 2
0.678	Remote Similarity	NPD7699	Phase 2
0.6778	Remote Similarity	NPD6674	Discontinued
0.6776	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7028	Phase 2
0.6771	Remote Similarity	NPD7608	Discontinued
0.6758	Remote Similarity	NPD6667	Approved
0.6758	Remote Similarity	NPD6666	Approved
0.6755	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3705	Approved
0.6739	Remote Similarity	NPD7526	Approved
0.6739	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD52	Approved
0.6738	Remote Similarity	NPD7411	Suspended
0.6738	Remote Similarity	NPD7110	Phase 1
0.6738	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7075	Discontinued
0.6736	Remote Similarity	NPD2969	Approved
0.6736	Remote Similarity	NPD2970	Approved
0.6735	Remote Similarity	NPD5557	Phase 1
0.6726	Remote Similarity	NPD8067	Phase 3
0.6723	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5977	Approved
0.672	Remote Similarity	NPD5978	Approved

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