NPASS Compound

Structure

CID3448 OpenBabel06191715322D 35 40 0 0 1 0 0 0 0 0999 V2000 -5.6876 0.2578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2937 1.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3962 2.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 1.7334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6347 0.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2409 2.1258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0908 3.4206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5520 2.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6971 1.9096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4110 -1.6259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8892 2.3671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7239 -1.6259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 0.9644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0908 1.7334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9114 1.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 3.4206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1611 2.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5674 -2.1129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9613 1.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4110 -0.6518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1534 1.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7239 -0.6518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1227 0.5096 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6894 1.1060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5674 -0.1647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3649 0.7880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0074 -0.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3962 0.8899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8585 1.6466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5520 4.2641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8120 3.3918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5674 -3.0870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1154 1.5265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8379 -0.7274 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 5 1 0 0 0 0 1 13 2 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 19 1 0 0 0 0 10 18 2 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 2 0 0 0 0 12 18 1 0 0 0 0 12 22 2 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 33 1 0 0 0 0 22 25 1 0 0 0 0 22 35 1 0 0 0 0 23 13 1 1 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 25 26 1 0 0 0 0 26 28 2 0 0 0 0 27 34 2 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.11
Volume:	466.126
LogP:	5.41
LogD:	2.963
LogS:	-5.645
# Rotatable Bonds:	1
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	3.395
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.14
MDCK Permeability:	7.822831321391277e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.276
20% Bioavailability (F20%):	0.078
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	92.24471282958984%
Volume Distribution (VD):	0.568
Pgp-substrate:	6.569160461425781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.551
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.795
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.753
CYP2D6-substrate:	0.443
CYP3A4-inhibitor:	0.424
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	4.046
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.532
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.948
Carcinogencity:	0.364
Eye Corrosion:	0.005
Eye Irritation:	0.924
Respiratory Toxicity:	0.2

Download Data

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

Natural Product: NPC3448

Natural Product ID:	NPC3448
*Common Name:**	Hopeafuran
IUPAC Name:	n.a.
Synonyms:	Hopeafuran
Standard InCHIKey:	HMIFNEKPRFKIQX-QHCPKHFHSA-N
Standard InCHI:	InChI=1S/C28H18O7/c29-15-5-1-13(2-6-15)23-24-19(9-17(31)11-21(24)33)26-25-20(27(23)34)10-18(32)12-22(25)35-28(26)14-3-7-16(30)8-4-14/h1-12,23,29-33H/t23-/m0/s1
SMILES:	c1cc(ccc1[C@H]1c2c(-c3c4c(cc(cc4oc3c3ccc(cc3)O)O)C1=O)cc(cc2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939429
PubChem CID:	57397234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	Barks	n.a.	n.a.	PMID[22209731]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13778	Melandrium turkestanicum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14476	Sterculia alata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14958	Duguetia eximia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17995	Xeromphis spinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16805	Senecio cisplatinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16691	Viguiera radula	Species	Asteraceae	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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	105000.0	nM	PMID[559431]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	=	142000.0	nM	PMID[559431]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	6900.0	nM	PMID[559431]

☑ 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 NPC3448 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	517
0.1-0.2	2126
0.2-0.3	4485
0.3-0.4	11847
0.4-0.5	6128
0.5-0.6	4386
0.6-0.7	5693
0.7-0.8	5254
0.8-0.85	1966
0.85-0.9	278
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477239
0.9494	High Similarity	NPC474591
0.9295	High Similarity	NPC137100
0.9161	High Similarity	NPC193976
0.9161	High Similarity	NPC23668
0.9108	High Similarity	NPC99199
0.9103	High Similarity	NPC207624
0.9103	High Similarity	NPC142308
0.9045	High Similarity	NPC235333
0.9038	High Similarity	NPC106372
0.9038	High Similarity	NPC115324
0.9038	High Similarity	NPC58668
0.9012	High Similarity	NPC169471
0.8994	High Similarity	NPC268360
0.8987	High Similarity	NPC297531
0.8987	High Similarity	NPC148938
0.8987	High Similarity	NPC213936
0.8982	High Similarity	NPC475783
0.8951	High Similarity	NPC159508
0.8938	High Similarity	NPC472877
0.8902	High Similarity	NPC286230
0.8902	High Similarity	NPC253730
0.8896	High Similarity	NPC155144
0.8875	High Similarity	NPC212967
0.8875	High Similarity	NPC164110
0.8875	High Similarity	NPC96342
0.8875	High Similarity	NPC246647
0.8868	High Similarity	NPC254351
0.8854	High Similarity	NPC230713
0.8854	High Similarity	NPC167576
0.8854	High Similarity	NPC78335
0.8834	High Similarity	NPC38591
0.8812	High Similarity	NPC180924
0.8805	High Similarity	NPC472462
0.8805	High Similarity	NPC72370
0.8805	High Similarity	NPC214632
0.8797	High Similarity	NPC170169
0.879	High Similarity	NPC178202
0.8782	High Similarity	NPC77903
0.8782	High Similarity	NPC17101
0.8782	High Similarity	NPC17816
0.8774	High Similarity	NPC230943
0.875	High Similarity	NPC226656
0.875	High Similarity	NPC198490
0.875	High Similarity	NPC66508
0.8726	High Similarity	NPC135325
0.8726	High Similarity	NPC106328
0.8726	High Similarity	NPC35150
0.8718	High Similarity	NPC210826
0.871	High Similarity	NPC302181
0.8704	High Similarity	NPC18699
0.8704	High Similarity	NPC55443
0.8704	High Similarity	NPC195167
0.8696	High Similarity	NPC309648
0.869	High Similarity	NPC59491
0.869	High Similarity	NPC24748
0.8688	High Similarity	NPC213608
0.8688	High Similarity	NPC1477
0.8688	High Similarity	NPC183874
0.8679	High Similarity	NPC156244
0.8671	High Similarity	NPC65775
0.8671	High Similarity	NPC10027
0.8671	High Similarity	NPC226644
0.8671	High Similarity	NPC473978
0.8671	High Similarity	NPC221868
0.8671	High Similarity	NPC37208
0.8671	High Similarity	NPC37226
0.8662	High Similarity	NPC130581
0.8662	High Similarity	NPC12148
0.8659	High Similarity	NPC143402
0.8659	High Similarity	NPC261896
0.8654	High Similarity	NPC98926
0.865	High Similarity	NPC292863
0.865	High Similarity	NPC184326
0.8645	High Similarity	NPC53192
0.8642	High Similarity	NPC201127
0.8642	High Similarity	NPC65504
0.8639	High Similarity	NPC300657
0.8634	High Similarity	NPC201227
0.8634	High Similarity	NPC258474
0.8631	High Similarity	NPC174700
0.8631	High Similarity	NPC28589
0.8631	High Similarity	NPC248593
0.8625	High Similarity	NPC40356
0.8625	High Similarity	NPC5871
0.8625	High Similarity	NPC154683
0.8625	High Similarity	NPC67654
0.8625	High Similarity	NPC41326
0.8625	High Similarity	NPC253872
0.8623	High Similarity	NPC53252
0.8608	High Similarity	NPC272194
0.8599	High Similarity	NPC51641
0.8599	High Similarity	NPC300267
0.8598	High Similarity	NPC301256
0.8598	High Similarity	NPC312273
0.8598	High Similarity	NPC304387
0.8598	High Similarity	NPC18380
0.8598	High Similarity	NPC137232
0.859	High Similarity	NPC225884
0.8589	High Similarity	NPC324736
0.8589	High Similarity	NPC177650
0.8589	High Similarity	NPC40583
0.8589	High Similarity	NPC244750
0.8588	High Similarity	NPC101991
0.8581	High Similarity	NPC49108
0.858	High Similarity	NPC160015
0.858	High Similarity	NPC61112
0.858	High Similarity	NPC198489
0.858	High Similarity	NPC247677
0.858	High Similarity	NPC473834
0.8571	High Similarity	NPC329844
0.8563	High Similarity	NPC50394
0.8562	High Similarity	NPC116604
0.8562	High Similarity	NPC111112
0.8562	High Similarity	NPC222713
0.8562	High Similarity	NPC149085
0.8562	High Similarity	NPC305965
0.8562	High Similarity	NPC138299
0.8562	High Similarity	NPC258249
0.8562	High Similarity	NPC67322
0.8553	High Similarity	NPC288840
0.8553	High Similarity	NPC39929
0.8553	High Similarity	NPC291746
0.8553	High Similarity	NPC296030
0.8545	High Similarity	NPC473011
0.8545	High Similarity	NPC193998
0.8545	High Similarity	NPC473012
0.8544	High Similarity	NPC150215
0.8537	High Similarity	NPC312993
0.8537	High Similarity	NPC472060
0.8537	High Similarity	NPC115432
0.8537	High Similarity	NPC186325
0.8537	High Similarity	NPC472052
0.8537	High Similarity	NPC470342
0.8537	High Similarity	NPC260296
0.8528	High Similarity	NPC287789
0.8528	High Similarity	NPC296957
0.8528	High Similarity	NPC271741
0.8528	High Similarity	NPC260902
0.8526	High Similarity	NPC310340
0.8516	High Similarity	NPC275734
0.8512	High Similarity	NPC202470
0.8509	High Similarity	NPC263676
0.8503	High Similarity	NPC53640
0.85	High Similarity	NPC470107
0.85	High Similarity	NPC295036
0.85	High Similarity	NPC227122
0.85	High Similarity	NPC13282
0.8494	Intermediate Similarity	NPC155640
0.8494	Intermediate Similarity	NPC109180
0.8494	Intermediate Similarity	NPC133065
0.8494	Intermediate Similarity	NPC473009
0.8494	Intermediate Similarity	NPC290160
0.8491	Intermediate Similarity	NPC152233
0.8488	Intermediate Similarity	NPC121888
0.8485	Intermediate Similarity	NPC231758
0.8485	Intermediate Similarity	NPC189552
0.8485	Intermediate Similarity	NPC273467
0.8481	Intermediate Similarity	NPC299011
0.8476	Intermediate Similarity	NPC476350
0.8476	Intermediate Similarity	NPC476349
0.8476	Intermediate Similarity	NPC226287
0.8471	Intermediate Similarity	NPC251182
0.8471	Intermediate Similarity	NPC19896
0.8471	Intermediate Similarity	NPC172182
0.8471	Intermediate Similarity	NPC262935
0.8466	Intermediate Similarity	NPC32867
0.8466	Intermediate Similarity	NPC56049
0.8466	Intermediate Similarity	NPC13879
0.8466	Intermediate Similarity	NPC69531
0.8466	Intermediate Similarity	NPC54830
0.8462	Intermediate Similarity	NPC14871
0.8462	Intermediate Similarity	NPC476641
0.8457	Intermediate Similarity	NPC122365
0.8457	Intermediate Similarity	NPC208806
0.8457	Intermediate Similarity	NPC178964
0.8457	Intermediate Similarity	NPC71061
0.8457	Intermediate Similarity	NPC121568
0.8457	Intermediate Similarity	NPC72425
0.8457	Intermediate Similarity	NPC290830
0.8457	Intermediate Similarity	NPC280530
0.8457	Intermediate Similarity	NPC303485
0.8457	Intermediate Similarity	NPC95842
0.8457	Intermediate Similarity	NPC194593
0.8452	Intermediate Similarity	NPC470704
0.8447	Intermediate Similarity	NPC474417
0.8447	Intermediate Similarity	NPC149526
0.8443	Intermediate Similarity	NPC39306
0.8443	Intermediate Similarity	NPC29411
0.8443	Intermediate Similarity	NPC473010
0.8443	Intermediate Similarity	NPC136641
0.8443	Intermediate Similarity	NPC38914
0.8439	Intermediate Similarity	NPC47883
0.8438	Intermediate Similarity	NPC288036
0.8438	Intermediate Similarity	NPC226578
0.8438	Intermediate Similarity	NPC329933
0.8438	Intermediate Similarity	NPC100985
0.8438	Intermediate Similarity	NPC97029
0.8438	Intermediate Similarity	NPC158338
0.8438	Intermediate Similarity	NPC97028

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 NPC3448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	473
0.1-0.2	1005
0.2-0.3	1626
0.3-0.4	2822
0.4-0.5	1818
0.5-0.6	961
0.6-0.7	291
0.7-0.8	119
0.8-0.85	32
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8994	High Similarity	NPD3749	Approved
0.8405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD2344	Approved
0.8302	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7411	Suspended
0.8165	Intermediate Similarity	NPD3750	Approved
0.8153	Intermediate Similarity	NPD1549	Phase 2
0.8133	Intermediate Similarity	NPD7768	Phase 2
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8113	Intermediate Similarity	NPD2309	Approved
0.8089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1510	Phase 2
0.8075	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7473	Discontinued
0.8024	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD1511	Approved
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD3226	Approved
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7935	Intermediate Similarity	NPD1240	Approved
0.7933	Intermediate Similarity	NPD4287	Approved
0.7925	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1512	Approved
0.7911	Intermediate Similarity	NPD2796	Approved
0.7904	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2801	Approved
0.7901	Intermediate Similarity	NPD7390	Discontinued
0.7882	Intermediate Similarity	NPD5494	Approved
0.7848	Intermediate Similarity	NPD3748	Approved
0.7848	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD1934	Approved
0.7834	Intermediate Similarity	NPD1607	Approved
0.7831	Intermediate Similarity	NPD4380	Phase 2
0.7816	Intermediate Similarity	NPD3818	Discontinued
0.7811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6166	Phase 2
0.7803	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2800	Approved
0.7764	Intermediate Similarity	NPD1243	Approved
0.775	Intermediate Similarity	NPD1471	Phase 3
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2534	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.774	Intermediate Similarity	NPD6559	Discontinued
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7688	Intermediate Similarity	NPD5408	Approved
0.7688	Intermediate Similarity	NPD5406	Approved
0.7688	Intermediate Similarity	NPD5405	Approved
0.7688	Intermediate Similarity	NPD5404	Approved
0.7684	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5844	Phase 1
0.7661	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD920	Approved
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1247	Approved
0.7625	Intermediate Similarity	NPD2799	Discontinued
0.7622	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3764	Approved
0.7578	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD6099	Approved
0.7576	Intermediate Similarity	NPD6799	Approved
0.7544	Intermediate Similarity	NPD2296	Approved
0.753	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7486	Intermediate Similarity	NPD7229	Phase 3
0.7484	Intermediate Similarity	NPD1470	Approved
0.7484	Intermediate Similarity	NPD943	Approved
0.7469	Intermediate Similarity	NPD1551	Phase 2
0.7459	Intermediate Similarity	NPD8313	Approved
0.7459	Intermediate Similarity	NPD8312	Approved
0.7456	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4908	Phase 1
0.7442	Intermediate Similarity	NPD5402	Approved
0.7442	Intermediate Similarity	NPD3817	Phase 2
0.743	Intermediate Similarity	NPD7074	Phase 3
0.7427	Intermediate Similarity	NPD6801	Discontinued
0.7423	Intermediate Similarity	NPD2346	Discontinued
0.7416	Intermediate Similarity	NPD3751	Discontinued
0.7414	Intermediate Similarity	NPD919	Approved
0.7403	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7054	Approved
0.7362	Intermediate Similarity	NPD2935	Discontinued
0.7358	Intermediate Similarity	NPD3268	Approved
0.7358	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5403	Approved
0.7333	Intermediate Similarity	NPD7472	Approved
0.733	Intermediate Similarity	NPD7199	Phase 2
0.7318	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6797	Phase 2
0.7293	Intermediate Similarity	NPD5953	Discontinued
0.7289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7003	Approved
0.7288	Intermediate Similarity	NPD3787	Discontinued
0.7288	Intermediate Similarity	NPD6808	Phase 2
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1203	Approved
0.7258	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7251	Discontinued
0.725	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7247	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7241	Intermediate Similarity	NPD4288	Approved
0.7226	Intermediate Similarity	NPD1201	Approved
0.7225	Intermediate Similarity	NPD6279	Approved
0.7225	Intermediate Similarity	NPD6280	Approved
0.7222	Intermediate Similarity	NPD7177	Discontinued
0.7219	Intermediate Similarity	NPD5401	Approved
0.7215	Intermediate Similarity	NPD2798	Approved
0.7213	Intermediate Similarity	NPD7808	Phase 3
0.7191	Intermediate Similarity	NPD5710	Approved
0.7191	Intermediate Similarity	NPD5711	Approved
0.7188	Intermediate Similarity	NPD4625	Phase 3
0.7188	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5761	Phase 2
0.7184	Intermediate Similarity	NPD5760	Phase 2
0.7178	Intermediate Similarity	NPD6651	Approved
0.7176	Intermediate Similarity	NPD6273	Approved
0.7118	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1610	Phase 2
0.7088	Intermediate Similarity	NPD7286	Phase 2
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7071	Intermediate Similarity	NPD8151	Discontinued
0.707	Intermediate Similarity	NPD1608	Approved
0.7065	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2797	Approved
0.7044	Intermediate Similarity	NPD3267	Approved
0.7044	Intermediate Similarity	NPD3266	Approved
0.7029	Intermediate Similarity	NPD37	Approved
0.7022	Intermediate Similarity	NPD6234	Discontinued
0.7017	Intermediate Similarity	NPD2403	Approved
0.701	Intermediate Similarity	NPD6779	Approved
0.701	Intermediate Similarity	NPD6780	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD6778	Approved
0.7006	Intermediate Similarity	NPD4967	Phase 2
0.7006	Intermediate Similarity	NPD4965	Approved
0.7006	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4966	Approved
0.7005	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3225	Approved
0.6981	Remote Similarity	NPD1876	Approved
0.6979	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4361	Phase 2
0.6962	Remote Similarity	NPD9717	Approved
0.6954	Remote Similarity	NPD7458	Discontinued
0.6954	Remote Similarity	NPD7871	Phase 2
0.6954	Remote Similarity	NPD7870	Phase 2
0.6949	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4360	Phase 2
0.6927	Remote Similarity	NPD4363	Phase 3
0.6923	Remote Similarity	NPD2654	Approved
0.6918	Remote Similarity	NPD4749	Approved
0.6914	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6832	Phase 2
0.6909	Remote Similarity	NPD447	Suspended
0.6904	Remote Similarity	NPD7435	Discontinued
0.6904	Remote Similarity	NPD7697	Approved
0.6904	Remote Similarity	NPD7696	Phase 3
0.6904	Remote Similarity	NPD7698	Approved
0.6886	Remote Similarity	NPD4308	Phase 3
0.6886	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD17	Approved
0.6872	Remote Similarity	NPD6971	Discontinued
0.6865	Remote Similarity	NPD1729	Discontinued
0.6859	Remote Similarity	NPD1548	Phase 1
0.6856	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2861	Phase 2
0.6848	Remote Similarity	NPD7228	Approved
0.6833	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD411	Approved
0.6823	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD230	Phase 1
0.6807	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8455	Phase 2
0.6792	Remote Similarity	NPD422	Phase 1
0.6789	Remote Similarity	NPD8150	Discontinued
0.6786	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7701	Phase 2
0.6753	Remote Similarity	NPD6534	Approved
0.6753	Remote Similarity	NPD6535	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