NPASS Compound

Structure

NPC312006 OpenBabel07101718312D 38 43 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1854 -1.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -2.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 0.1910 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 12 2 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 15 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 10 36 1 0 0 0 0 11 1 1 1 0 0 0 11 22 1 0 0 0 0 11 37 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 25 2 0 0 0 0 16 19 2 0 0 0 0 16 35 1 0 0 0 0 17 18 2 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 36 1 0 0 0 0 20 21 2 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 23 24 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 0 0 0 0 24 30 1 6 0 0 0 25 38 1 0 0 0 0 26 31 2 0 0 0 0 26 34 1 0 0 0 0 27 37 1 0 0 0 0 27 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.15
Volume:	497.174
LogP:	2.923
LogD:	2.442
LogS:	-4.732
# Rotatable Bonds:	5
TPSA:	142.37
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.093
Fsp3:	0.37
Lipinski Rule-of-5:	Rejected
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:	-5.784
MDCK Permeability:	3.6031757190357894e-05
Pgp-inhibitor:	0.1
Pgp-substrate:	0.434
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	84.09951782226562%
Volume Distribution (VD):	0.74
Pgp-substrate:	2.5438895225524902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.35
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.315
CYP2C19-substrate:	0.194
CYP2C9-inhibitor:	0.366
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.846
CYP3A4-inhibitor:	0.778
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	11.679
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.758
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.102
Skin Sensitization:	0.044
Carcinogencity:	0.923
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.497

Download Data

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

Natural Product: NPC312006

Natural Product ID:	NPC312006
*Common Name:**	Patentiflorin B
IUPAC Name:	9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:	patentiflorin B
Standard InCHIKey:	NLWUWPJUIJTHAN-HJTDAGSESA-N
Standard InCHI:	InChI=1S/C27H26O11/c1-11-22(28)23(29)24(30)27(37-11)38-25-14-8-18(33-3)17(32-2)7-13(14)20(21-15(25)9-34-26(21)31)12-4-5-16-19(6-12)36-10-35-16/h4-8,11,22-24,27-30H,9-10H2,1-3H3/t11-,22+,23+,24-,27+/m0/s1
SMILES:	COc1cc2c(O[C@H]3O[C@@H](C)[C@H]([C@H]([C@@H]3O)O)O)c3COC(=O)c3c(c2cc1OC)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458905
PubChem CID:	11478022
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*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
NPO20590	Justicia patentiflora	Species	Acanthaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[15921419]
NPO20590	Justicia patentiflora	Species	Acanthaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.0	nM	PMID[549446]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	300.0	nM	PMID[549446]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	250.0	nM	PMID[549446]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[549447]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1420.0	nM	PMID[549447]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[549447]

☑ 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 NPC312006 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	378
0.1-0.2	1594
0.2-0.3	3251
0.3-0.4	8182
0.4-0.5	9692
0.5-0.6	4903
0.6-0.7	6844
0.7-0.8	6863
0.8-0.85	898
0.85-0.9	67
0.9-0.95	9
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC20114
1.0	High Similarity	NPC471922
1.0	High Similarity	NPC114550
1.0	High Similarity	NPC471920
1.0	High Similarity	NPC471921
1.0	High Similarity	NPC474075
1.0	High Similarity	NPC292712
1.0	High Similarity	NPC129930
0.9756	High Similarity	NPC35266
0.9697	High Similarity	NPC161609
0.9697	High Similarity	NPC275690
0.9693	High Similarity	NPC184624
0.9634	High Similarity	NPC193377
0.9627	High Similarity	NPC471923
0.9568	High Similarity	NPC475453
0.9568	High Similarity	NPC473531
0.9524	High Similarity	NPC167045
0.9524	High Similarity	NPC114120
0.9412	High Similarity	NPC313063
0.9412	High Similarity	NPC286301
0.9394	High Similarity	NPC473697
0.9333	High Similarity	NPC52598
0.9321	High Similarity	NPC116838
0.9321	High Similarity	NPC22130
0.925	High Similarity	NPC239113
0.925	High Similarity	NPC115123
0.9157	High Similarity	NPC117911
0.9152	High Similarity	NPC474042
0.9152	High Similarity	NPC174734
0.9091	High Similarity	NPC222531
0.9085	High Similarity	NPC198796
0.908	High Similarity	NPC78944
0.9074	High Similarity	NPC19600
0.9024	High Similarity	NPC115624
0.9018	High Similarity	NPC474043
0.9	High Similarity	NPC196771
0.8994	High Similarity	NPC316539
0.8957	High Similarity	NPC143328
0.8953	High Similarity	NPC208797
0.8953	High Similarity	NPC53680
0.8909	High Similarity	NPC152424
0.8909	High Similarity	NPC15212
0.8909	High Similarity	NPC100465
0.8889	High Similarity	NPC79736
0.8889	High Similarity	NPC67629
0.8882	High Similarity	NPC474442
0.8882	High Similarity	NPC199357
0.8876	High Similarity	NPC135370
0.8875	High Similarity	NPC475722
0.8869	High Similarity	NPC79322
0.8855	High Similarity	NPC22324
0.8837	High Similarity	NPC47191
0.8837	High Similarity	NPC267549
0.8834	High Similarity	NPC234730
0.883	High Similarity	NPC146803
0.8824	High Similarity	NPC38438
0.8807	High Similarity	NPC205721
0.8802	High Similarity	NPC116759
0.8802	High Similarity	NPC14294
0.8802	High Similarity	NPC17432
0.878	High Similarity	NPC109765
0.8773	High Similarity	NPC54179
0.8757	High Similarity	NPC298847
0.875	High Similarity	NPC105591
0.875	High Similarity	NPC178281
0.8735	High Similarity	NPC96593
0.8735	High Similarity	NPC119910
0.8727	High Similarity	NPC202495
0.8727	High Similarity	NPC19947
0.8727	High Similarity	NPC207584
0.8715	High Similarity	NPC476358
0.8698	High Similarity	NPC306475
0.8698	High Similarity	NPC83049
0.8698	High Similarity	NPC118162
0.8698	High Similarity	NPC320471
0.8696	High Similarity	NPC127827
0.8683	High Similarity	NPC258322
0.8683	High Similarity	NPC288149
0.8683	High Similarity	NPC191352
0.8678	High Similarity	NPC212290
0.8675	High Similarity	NPC125713
0.8671	High Similarity	NPC297574
0.8667	High Similarity	NPC32373
0.8667	High Similarity	NPC237946
0.8667	High Similarity	NPC473900
0.8655	High Similarity	NPC298778
0.865	High Similarity	NPC118332
0.8647	High Similarity	NPC185498
0.8647	High Similarity	NPC311912
0.8642	High Similarity	NPC158635
0.8642	High Similarity	NPC229882
0.8631	High Similarity	NPC278329
0.8631	High Similarity	NPC56735
0.8631	High Similarity	NPC146837
0.8631	High Similarity	NPC61594
0.8623	High Similarity	NPC150943
0.8623	High Similarity	NPC474770
0.8623	High Similarity	NPC65784
0.8623	High Similarity	NPC91634
0.8623	High Similarity	NPC268718
0.8614	High Similarity	NPC133984
0.8613	High Similarity	NPC470667
0.8613	High Similarity	NPC68381
0.8613	High Similarity	NPC199533
0.8613	High Similarity	NPC470454
0.8613	High Similarity	NPC186800
0.8606	High Similarity	NPC186316
0.8598	High Similarity	NPC137813
0.8596	High Similarity	NPC88557
0.8596	High Similarity	NPC473202
0.8588	High Similarity	NPC241847
0.858	High Similarity	NPC111785
0.858	High Similarity	NPC476203
0.858	High Similarity	NPC121290
0.858	High Similarity	NPC147596
0.8571	High Similarity	NPC114257
0.8571	High Similarity	NPC277710
0.8571	High Similarity	NPC80956
0.8571	High Similarity	NPC216916
0.8571	High Similarity	NPC153578
0.8571	High Similarity	NPC299149
0.8563	High Similarity	NPC469397
0.8563	High Similarity	NPC478269
0.8563	High Similarity	NPC475054
0.8563	High Similarity	NPC473713
0.8563	High Similarity	NPC241600
0.8563	High Similarity	NPC472723
0.8563	High Similarity	NPC324220
0.8563	High Similarity	NPC173726
0.8563	High Similarity	NPC475233
0.8563	High Similarity	NPC312630
0.8555	High Similarity	NPC263119
0.8555	High Similarity	NPC34436
0.8555	High Similarity	NPC219600
0.8555	High Similarity	NPC166674
0.8555	High Similarity	NPC46640
0.8555	High Similarity	NPC85368
0.8554	High Similarity	NPC228357
0.8554	High Similarity	NPC478055
0.8554	High Similarity	NPC261090
0.8547	High Similarity	NPC477572
0.8547	High Similarity	NPC477571
0.8547	High Similarity	NPC179240
0.8547	High Similarity	NPC477573
0.8547	High Similarity	NPC313304
0.8545	High Similarity	NPC185103
0.8537	High Similarity	NPC36130
0.8537	High Similarity	NPC134905
0.8523	High Similarity	NPC475161
0.8523	High Similarity	NPC188217
0.8523	High Similarity	NPC477860
0.8521	High Similarity	NPC212099
0.8521	High Similarity	NPC101116
0.8521	High Similarity	NPC285108
0.8521	High Similarity	NPC216752
0.8521	High Similarity	NPC33298
0.8519	High Similarity	NPC181464
0.8512	High Similarity	NPC328093
0.8506	High Similarity	NPC474345
0.8506	High Similarity	NPC469438
0.8506	High Similarity	NPC63105
0.8503	High Similarity	NPC167098
0.8503	High Similarity	NPC181168
0.8503	High Similarity	NPC296044
0.8503	High Similarity	NPC163527
0.8503	High Similarity	NPC115281
0.85	High Similarity	NPC264302
0.8497	Intermediate Similarity	NPC111536
0.8497	Intermediate Similarity	NPC5029
0.8497	Intermediate Similarity	NPC76128
0.8497	Intermediate Similarity	NPC271385
0.8497	Intermediate Similarity	NPC30432
0.8494	Intermediate Similarity	NPC10205
0.8494	Intermediate Similarity	NPC472835
0.8488	Intermediate Similarity	NPC259905
0.8488	Intermediate Similarity	NPC191653
0.8485	Intermediate Similarity	NPC61604
0.8485	Intermediate Similarity	NPC299706
0.8485	Intermediate Similarity	NPC115466
0.8485	Intermediate Similarity	NPC245948
0.8485	Intermediate Similarity	NPC245615
0.848	Intermediate Similarity	NPC178851
0.8476	Intermediate Similarity	NPC13985
0.8476	Intermediate Similarity	NPC210642
0.8475	Intermediate Similarity	NPC129533
0.8475	Intermediate Similarity	NPC123259
0.8471	Intermediate Similarity	NPC45943
0.8471	Intermediate Similarity	NPC25889
0.8466	Intermediate Similarity	NPC84494
0.8466	Intermediate Similarity	NPC245059
0.8466	Intermediate Similarity	NPC24193
0.8462	Intermediate Similarity	NPC478267
0.8462	Intermediate Similarity	NPC319749
0.8462	Intermediate Similarity	NPC469889
0.8462	Intermediate Similarity	NPC99968
0.8457	Intermediate Similarity	NPC475246
0.8448	Intermediate Similarity	NPC88560
0.8448	Intermediate Similarity	NPC175230
0.8448	Intermediate Similarity	NPC172033
0.8448	Intermediate Similarity	NPC473550

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 NPC312006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	891
0.2-0.3	1650
0.3-0.4	2660
0.4-0.5	1967
0.5-0.6	1059
0.6-0.7	445
0.7-0.8	129
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8706	High Similarity	NPD5844	Phase 1
0.8667	High Similarity	NPD4967	Phase 2
0.8667	High Similarity	NPD4965	Approved
0.8667	High Similarity	NPD4966	Approved
0.8647	High Similarity	NPD7228	Approved
0.8563	High Similarity	NPD6234	Discontinued
0.8485	Intermediate Similarity	NPD37	Approved
0.8462	Intermediate Similarity	NPD7199	Phase 2
0.8448	Intermediate Similarity	NPD6559	Discontinued
0.8448	Intermediate Similarity	NPD7240	Approved
0.8352	Intermediate Similarity	NPD8313	Approved
0.8352	Intermediate Similarity	NPD8312	Approved
0.8323	Intermediate Similarity	NPD8455	Phase 2
0.8304	Intermediate Similarity	NPD6232	Discontinued
0.8256	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD3818	Discontinued
0.8161	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD7074	Phase 3
0.811	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6674	Discontinued
0.8084	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7054	Approved
0.8056	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7472	Approved
0.7964	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6166	Phase 2
0.7895	Intermediate Similarity	NPD1465	Phase 2
0.7889	Intermediate Similarity	NPD7808	Phase 3
0.7877	Intermediate Similarity	NPD6797	Phase 2
0.7874	Intermediate Similarity	NPD5494	Approved
0.7861	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7685	Pre-registration
0.7833	Intermediate Similarity	NPD7251	Discontinued
0.7829	Intermediate Similarity	NPD6959	Discontinued
0.7801	Intermediate Similarity	NPD7680	Approved
0.7795	Intermediate Similarity	NPD7783	Phase 2
0.7795	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7791	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3817	Phase 2
0.7733	Intermediate Similarity	NPD1934	Approved
0.7727	Intermediate Similarity	NPD8127	Discontinued
0.7711	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD8151	Discontinued
0.7661	Intermediate Similarity	NPD3226	Approved
0.7636	Intermediate Similarity	NPD2346	Discontinued
0.7617	Intermediate Similarity	NPD7435	Discontinued
0.7602	Intermediate Similarity	NPD1653	Approved
0.7588	Intermediate Similarity	NPD6273	Approved
0.7586	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3787	Discontinued
0.7572	Intermediate Similarity	NPD7411	Suspended
0.7558	Intermediate Similarity	NPD7458	Discontinued
0.7557	Intermediate Similarity	NPD7075	Discontinued
0.7552	Intermediate Similarity	NPD6777	Approved
0.7552	Intermediate Similarity	NPD6780	Approved
0.7552	Intermediate Similarity	NPD6776	Approved
0.7552	Intermediate Similarity	NPD6778	Approved
0.7552	Intermediate Similarity	NPD6779	Approved
0.7552	Intermediate Similarity	NPD6782	Approved
0.7552	Intermediate Similarity	NPD6781	Approved
0.7545	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7266	Discontinued
0.7529	Intermediate Similarity	NPD2533	Approved
0.7529	Intermediate Similarity	NPD2534	Approved
0.7529	Intermediate Similarity	NPD2532	Approved
0.7514	Intermediate Similarity	NPD4380	Phase 2
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.7514	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7486	Intermediate Similarity	NPD7229	Phase 3
0.7486	Intermediate Similarity	NPD2801	Approved
0.7474	Intermediate Similarity	NPD6823	Phase 2
0.7458	Intermediate Similarity	NPD3749	Approved
0.7449	Intermediate Similarity	NPD7999	Approved
0.7448	Intermediate Similarity	NPD4420	Approved
0.7443	Intermediate Similarity	NPD5402	Approved
0.7443	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1933	Approved
0.7429	Intermediate Similarity	NPD6801	Discontinued
0.7427	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7870	Phase 2
0.7398	Intermediate Similarity	NPD7871	Phase 2
0.7396	Intermediate Similarity	NPD3750	Approved
0.7387	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7874	Approved
0.7365	Intermediate Similarity	NPD2438	Suspended
0.7362	Intermediate Similarity	NPD6798	Discontinued
0.7347	Intermediate Similarity	NPD7697	Approved
0.7347	Intermediate Similarity	NPD7696	Phase 3
0.7347	Intermediate Similarity	NPD7698	Approved
0.734	Intermediate Similarity	NPD8150	Discontinued
0.7337	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7177	Discontinued
0.7321	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD919	Approved
0.7314	Intermediate Similarity	NPD6599	Discontinued
0.7314	Intermediate Similarity	NPD7028	Phase 2
0.7305	Intermediate Similarity	NPD3748	Approved
0.7296	Intermediate Similarity	NPD5006	Approved
0.7296	Intermediate Similarity	NPD5005	Approved
0.7292	Intermediate Similarity	NPD6535	Approved
0.7292	Intermediate Similarity	NPD6534	Approved
0.7286	Intermediate Similarity	NPD7701	Phase 2
0.7262	Intermediate Similarity	NPD5405	Approved
0.7262	Intermediate Similarity	NPD5406	Approved
0.7262	Intermediate Similarity	NPD5404	Approved
0.7262	Intermediate Similarity	NPD2935	Discontinued
0.7262	Intermediate Similarity	NPD5408	Approved
0.7258	Intermediate Similarity	NPD7039	Approved
0.7258	Intermediate Similarity	NPD7038	Approved
0.7256	Intermediate Similarity	NPD3764	Approved
0.7253	Intermediate Similarity	NPD3926	Phase 2
0.7249	Intermediate Similarity	NPD8434	Phase 2
0.7246	Intermediate Similarity	NPD7097	Phase 1
0.7241	Intermediate Similarity	NPD7930	Approved
0.7241	Intermediate Similarity	NPD5403	Approved
0.7229	Intermediate Similarity	NPD6355	Discontinued
0.7229	Intermediate Similarity	NPD447	Suspended
0.7225	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7212	Intermediate Similarity	NPD6233	Phase 2
0.7205	Intermediate Similarity	NPD1283	Approved
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.7195	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4110	Phase 3
0.7179	Intermediate Similarity	NPD7699	Phase 2
0.7179	Intermediate Similarity	NPD7700	Phase 2
0.7178	Intermediate Similarity	NPD7801	Approved
0.7169	Intermediate Similarity	NPD4060	Phase 1
0.7169	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2979	Phase 3
0.7169	Intermediate Similarity	NPD1613	Approved
0.7168	Intermediate Similarity	NPD6799	Approved
0.7168	Intermediate Similarity	NPD1511	Approved
0.7152	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6190	Approved
0.715	Intermediate Similarity	NPD6213	Phase 3
0.715	Intermediate Similarity	NPD6212	Phase 3
0.715	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1247	Approved
0.7129	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3705	Approved
0.7118	Intermediate Similarity	NPD5762	Approved
0.7118	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6004	Phase 3
0.7118	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6005	Phase 3
0.7118	Intermediate Similarity	NPD5763	Approved
0.7118	Intermediate Similarity	NPD6002	Phase 3
0.7115	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5710	Approved
0.7104	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1512	Approved
0.7076	Intermediate Similarity	NPD2424	Discontinued
0.7048	Intermediate Similarity	NPD2313	Discontinued
0.7048	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD920	Approved
0.7019	Intermediate Similarity	NPD1281	Approved
0.7019	Intermediate Similarity	NPD1091	Approved
0.7018	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5058	Phase 3
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD5125	Phase 3
0.7	Intermediate Similarity	NPD4308	Phase 3
0.6988	Remote Similarity	NPD4625	Phase 3
0.6988	Remote Similarity	NPD3027	Phase 3
0.6983	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7583	Approved
0.6977	Remote Similarity	NPD1549	Phase 2
0.6977	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7390	Discontinued
0.6964	Remote Similarity	NPD4140	Approved
0.6959	Remote Similarity	NPD4477	Approved
0.6959	Remote Similarity	NPD4476	Approved
0.6959	Remote Similarity	NPD1551	Phase 2
0.6959	Remote Similarity	NPD2796	Approved
0.6952	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7799	Discontinued
0.6951	Remote Similarity	NPD2797	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