NPASS Compound

Structure

NPC473622 OpenBabel07101719512D 42 45 0 0 1 0 0 0 0 0999 V2000 5.0832 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3581 -2.3146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3363 -2.3146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4891 0.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9783 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 4.8913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0136 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 4.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 4.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1664 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0136 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3192 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1664 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4720 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6248 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3192 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 0.4891 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.7776 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7776 0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7776 -1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 34 1 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 35 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 21 2 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 28 2 0 0 0 0 20 29 1 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 24 36 2 0 0 0 0 25 28 1 0 0 0 0 25 30 2 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 29 2 0 0 0 0 27 30 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 39 1 0 0 0 0 31 34 1 0 0 0 0 31 40 1 0 0 0 0 32 35 1 0 0 0 0 32 41 2 0 0 0 0 33 34 1 0 0 0 0 33 35 1 0 0 0 0 33 42 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.26
Volume:	606.948
LogP:	5.979
LogD:	2.699
LogS:	-4.484
# Rotatable Bonds:	9
TPSA:	128.97
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	3.669
Fsp3:	0.371
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.449
MDCK Permeability:	2.6120340407942422e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	99.93505096435547%
Volume Distribution (VD):	0.298
Pgp-substrate:	0.5262838006019592%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.971
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.625
CYP3A4-substrate:	0.935

ADMET: Excretion

Clearance (CL):	4.966
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.66
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.79
Maximum Recommended Daily Dose:	0.427
Skin Sensitization:	0.366
Carcinogencity:	0.213
Eye Corrosion:	0.003
Eye Irritation:	0.541
Respiratory Toxicity:	0.283

Download Data

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

Natural Product: NPC473622

Natural Product ID:	NPC473622
*Common Name:**	Corymbone A
IUPAC Name:	5-hydroxy-2,2,6,6-tetramethyl-4-[3-phenyl-1-[2,4,6-trihydroxy-3-methyl-5-(3-phenylpropanoyl)phenyl]propyl]cyclohex-4-ene-1,3-dione
Synonyms:
Standard InCHIKey:	OHJVUGQZZLSHQV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H38O7/c1-20-28(37)25(30(39)27(29(20)38)24(36)19-17-22-14-10-7-11-15-22)23(18-16-21-12-8-6-9-13-21)26-31(40)34(2,3)33(42)35(4,5)32(26)41/h6-15,23,37-40H,16-19H2,1-5H3
SMILES:	Cc1c(O)c(C(=O)CCc2ccccc2)c(c(c1O)C(C1=C(O)C(C)(C)C(=O)C(C1=O)(C)C)CCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447346
PubChem CID:	24878685
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO19917	Corymbia peltata	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[18412395]
NPO19917	Corymbia peltata	Species	Myrtaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3511	Individual Protein	Thyrotropin-releasing hormone receptor 2	Rattus norvegicus	IC50	=	23000.0	nM	PMID[551755]

☑ 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 NPC473622 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	364
0.1-0.2	1507
0.2-0.3	3219
0.3-0.4	8498
0.4-0.5	11138
0.5-0.6	5412
0.6-0.7	7231
0.7-0.8	4483
0.8-0.85	692
0.85-0.9	147
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9695	High Similarity	NPC475088
0.9104	High Similarity	NPC175738
0.9023	High Similarity	NPC73203
0.9015	High Similarity	NPC329205
0.9015	High Similarity	NPC116513
0.9015	High Similarity	NPC316625
0.9014	High Similarity	NPC271944
0.9014	High Similarity	NPC85393
0.9014	High Similarity	NPC110882
0.8947	High Similarity	NPC221777
0.8947	High Similarity	NPC473017
0.8939	High Similarity	NPC328983
0.8939	High Similarity	NPC267846
0.8913	High Similarity	NPC474110
0.8913	High Similarity	NPC44960
0.8881	High Similarity	NPC474998
0.8872	High Similarity	NPC103356
0.8872	High Similarity	NPC190043
0.8872	High Similarity	NPC105157
0.8872	High Similarity	NPC30501
0.8872	High Similarity	NPC98254
0.8872	High Similarity	NPC100067
0.8872	High Similarity	NPC162612
0.8872	High Similarity	NPC23126
0.8872	High Similarity	NPC72158
0.8872	High Similarity	NPC266689
0.8872	High Similarity	NPC169250
0.8849	High Similarity	NPC87723
0.8841	High Similarity	NPC191976
0.8819	High Similarity	NPC261271
0.8819	High Similarity	NPC475348
0.8806	High Similarity	NPC475553
0.8806	High Similarity	NPC21305
0.8806	High Similarity	NPC164894
0.8803	High Similarity	NPC451542
0.8803	High Similarity	NPC295712
0.8803	High Similarity	NPC474203
0.8803	High Similarity	NPC313047
0.8797	High Similarity	NPC62952
0.8777	High Similarity	NPC53001
0.8759	High Similarity	NPC152233
0.8723	High Similarity	NPC169452
0.8723	High Similarity	NPC470986
0.8723	High Similarity	NPC181560
0.8722	High Similarity	NPC475733
0.8722	High Similarity	NPC290466
0.8712	High Similarity	NPC65761
0.8712	High Similarity	NPC472029
0.8696	High Similarity	NPC282780
0.8696	High Similarity	NPC166480
0.8696	High Similarity	NPC270899
0.8681	High Similarity	NPC12402
0.8676	High Similarity	NPC259942
0.8671	High Similarity	NPC297600
0.8671	High Similarity	NPC174905
0.8671	High Similarity	NPC293545
0.8652	High Similarity	NPC242994
0.8652	High Similarity	NPC138099
0.8636	High Similarity	NPC91105
0.8636	High Similarity	NPC66252
0.8633	High Similarity	NPC249272
0.8633	High Similarity	NPC475917
0.8623	High Similarity	NPC139074
0.8623	High Similarity	NPC267205
0.8623	High Similarity	NPC213485
0.8623	High Similarity	NPC114183
0.8623	High Similarity	NPC40524
0.8613	High Similarity	NPC475042
0.8613	High Similarity	NPC275504
0.8609	High Similarity	NPC90497
0.8603	High Similarity	NPC476119
0.8603	High Similarity	NPC92624
0.8601	High Similarity	NPC193555
0.8581	High Similarity	NPC178484
0.8581	High Similarity	NPC476552
0.8581	High Similarity	NPC476551
0.8581	High Similarity	NPC476553
0.8561	High Similarity	NPC12070
0.8561	High Similarity	NPC196976
0.8561	High Similarity	NPC242895
0.8561	High Similarity	NPC215392
0.8561	High Similarity	NPC303737
0.8552	High Similarity	NPC471523
0.8552	High Similarity	NPC471473
0.8552	High Similarity	NPC282957
0.8552	High Similarity	NPC194949
0.8552	High Similarity	NPC471524
0.8531	High Similarity	NPC11056
0.8531	High Similarity	NPC265178
0.8531	High Similarity	NPC246638
0.8523	High Similarity	NPC43345
0.8521	High Similarity	NPC243528
0.8521	High Similarity	NPC251681
0.8521	High Similarity	NPC19622
0.8521	High Similarity	NPC112789
0.8511	High Similarity	NPC471905
0.8511	High Similarity	NPC53414
0.8511	High Similarity	NPC53206
0.85	High Similarity	NPC283590
0.85	High Similarity	NPC70859
0.85	High Similarity	NPC130899
0.85	High Similarity	NPC61153
0.8496	Intermediate Similarity	NPC133909
0.8496	Intermediate Similarity	NPC32032
0.8496	Intermediate Similarity	NPC309765
0.8493	Intermediate Similarity	NPC25844
0.8485	Intermediate Similarity	NPC149246
0.8485	Intermediate Similarity	NPC146642
0.8485	Intermediate Similarity	NPC229649
0.8483	Intermediate Similarity	NPC11700
0.8483	Intermediate Similarity	NPC227841
0.8478	Intermediate Similarity	NPC18798
0.8477	Intermediate Similarity	NPC56049
0.8477	Intermediate Similarity	NPC54830
0.8477	Intermediate Similarity	NPC192587
0.8472	Intermediate Similarity	NPC26238
0.8472	Intermediate Similarity	NPC40118
0.8472	Intermediate Similarity	NPC232021
0.8472	Intermediate Similarity	NPC126534
0.8472	Intermediate Similarity	NPC474961
0.8467	Intermediate Similarity	NPC324447
0.8467	Intermediate Similarity	NPC109123
0.8462	Intermediate Similarity	NPC275903
0.8456	Intermediate Similarity	NPC35
0.8456	Intermediate Similarity	NPC305965
0.8451	Intermediate Similarity	NPC322301
0.8451	Intermediate Similarity	NPC255801
0.8446	Intermediate Similarity	NPC477221
0.844	Intermediate Similarity	NPC264112
0.844	Intermediate Similarity	NPC118919
0.844	Intermediate Similarity	NPC254847
0.844	Intermediate Similarity	NPC194764
0.844	Intermediate Similarity	NPC65005
0.8429	Intermediate Similarity	NPC474117
0.8429	Intermediate Similarity	NPC474224
0.8429	Intermediate Similarity	NPC44437
0.8425	Intermediate Similarity	NPC476055
0.8421	Intermediate Similarity	NPC156139
0.8421	Intermediate Similarity	NPC143427
0.8421	Intermediate Similarity	NPC45438
0.8421	Intermediate Similarity	NPC224273
0.8421	Intermediate Similarity	NPC115159
0.8421	Intermediate Similarity	NPC19174
0.8421	Intermediate Similarity	NPC73532
0.8421	Intermediate Similarity	NPC267552
0.8414	Intermediate Similarity	NPC296752
0.8411	Intermediate Similarity	NPC79375
0.8411	Intermediate Similarity	NPC37253
0.8409	Intermediate Similarity	NPC294037
0.8394	Intermediate Similarity	NPC229894
0.8392	Intermediate Similarity	NPC477055
0.8392	Intermediate Similarity	NPC477056
0.8389	Intermediate Similarity	NPC48949
0.8382	Intermediate Similarity	NPC8745
0.8382	Intermediate Similarity	NPC473691
0.838	Intermediate Similarity	NPC213603
0.837	Intermediate Similarity	NPC13238
0.8369	Intermediate Similarity	NPC470210
0.8369	Intermediate Similarity	NPC103842
0.8369	Intermediate Similarity	NPC290803
0.8367	Intermediate Similarity	NPC143685
0.8358	Intermediate Similarity	NPC232708
0.8356	Intermediate Similarity	NPC10764
0.8346	Intermediate Similarity	NPC297186
0.8345	Intermediate Similarity	NPC137649
0.8345	Intermediate Similarity	NPC135524
0.8345	Intermediate Similarity	NPC14871
0.8344	Intermediate Similarity	NPC121568
0.8333	Intermediate Similarity	NPC188814
0.8333	Intermediate Similarity	NPC195262
0.8333	Intermediate Similarity	NPC477956
0.8333	Intermediate Similarity	NPC283429
0.8333	Intermediate Similarity	NPC117899
0.8322	Intermediate Similarity	NPC23870
0.8322	Intermediate Similarity	NPC471114
0.8322	Intermediate Similarity	NPC20210
0.8322	Intermediate Similarity	NPC153979
0.8312	Intermediate Similarity	NPC195136
0.8311	Intermediate Similarity	NPC300988
0.8311	Intermediate Similarity	NPC10990
0.8311	Intermediate Similarity	NPC290194
0.8311	Intermediate Similarity	NPC37709
0.831	Intermediate Similarity	NPC131039
0.831	Intermediate Similarity	NPC13575
0.831	Intermediate Similarity	NPC156092
0.8309	Intermediate Similarity	NPC477454
0.8309	Intermediate Similarity	NPC10926
0.8301	Intermediate Similarity	NPC1796
0.8301	Intermediate Similarity	NPC257166
0.8301	Intermediate Similarity	NPC208258
0.8299	Intermediate Similarity	NPC257236
0.8299	Intermediate Similarity	NPC271288
0.8299	Intermediate Similarity	NPC278175
0.8298	Intermediate Similarity	NPC470984
0.8288	Intermediate Similarity	NPC321629
0.8288	Intermediate Similarity	NPC321148
0.8288	Intermediate Similarity	NPC323884
0.8288	Intermediate Similarity	NPC326193
0.8284	Intermediate Similarity	NPC226275
0.8276	Intermediate Similarity	NPC259166

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 NPC473622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	929
0.2-0.3	1379
0.3-0.4	2767
0.4-0.5	2253
0.5-0.6	1065
0.6-0.7	332
0.7-0.8	85
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
0.8483	Intermediate Similarity	NPD7390	Discontinued
0.844	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD6651	Approved
0.8125	Intermediate Similarity	NPD5405	Approved
0.8125	Intermediate Similarity	NPD5404	Approved
0.8125	Intermediate Similarity	NPD5408	Approved
0.8125	Intermediate Similarity	NPD5406	Approved
0.8054	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD943	Approved
0.7959	Intermediate Similarity	NPD2800	Approved
0.7931	Intermediate Similarity	NPD1510	Phase 2
0.7902	Intermediate Similarity	NPD1240	Approved
0.7885	Intermediate Similarity	NPD7768	Phase 2
0.7883	Intermediate Similarity	NPD1201	Approved
0.7857	Intermediate Similarity	NPD7411	Suspended
0.7794	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1607	Approved
0.7792	Intermediate Similarity	NPD4380	Phase 2
0.7786	Intermediate Similarity	NPD1470	Approved
0.7764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7819	Suspended
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7703	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1164	Approved
0.7651	Intermediate Similarity	NPD1549	Phase 2
0.7643	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7075	Discontinued
0.7582	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6959	Discontinued
0.755	Intermediate Similarity	NPD3750	Approved
0.7532	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6232	Discontinued
0.7517	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD3749	Approved
0.745	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD2935	Discontinued
0.7389	Intermediate Similarity	NPD7458	Discontinued
0.7375	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1934	Approved
0.7357	Intermediate Similarity	NPD2932	Approved
0.7357	Intermediate Similarity	NPD3019	Approved
0.7351	Intermediate Similarity	NPD2344	Approved
0.7342	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6166	Phase 2
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.732	Intermediate Similarity	NPD7003	Approved
0.7312	Intermediate Similarity	NPD2801	Approved
0.7308	Intermediate Similarity	NPD1512	Approved
0.7285	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD6100	Approved
0.7284	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6801	Discontinued
0.7244	Intermediate Similarity	NPD2532	Approved
0.7244	Intermediate Similarity	NPD2533	Approved
0.7244	Intermediate Similarity	NPD2534	Approved
0.7241	Intermediate Similarity	NPD2798	Approved
0.7226	Intermediate Similarity	NPD3300	Phase 2
0.7219	Intermediate Similarity	NPD3748	Approved
0.7219	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5494	Approved
0.7194	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6799	Approved
0.7162	Intermediate Similarity	NPD3764	Approved
0.7161	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7135	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3882	Suspended
0.7113	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6020	Phase 2
0.7097	Intermediate Similarity	NPD8166	Discontinued
0.7083	Intermediate Similarity	NPD3972	Approved
0.7059	Intermediate Similarity	NPD4750	Phase 3
0.7059	Intermediate Similarity	NPD7074	Phase 3
0.705	Intermediate Similarity	NPD5951	Approved
0.7047	Intermediate Similarity	NPD2313	Discontinued
0.7047	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD846	Approved
0.7045	Intermediate Similarity	NPD940	Approved
0.7032	Intermediate Similarity	NPD1243	Approved
0.7012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD5844	Phase 1
0.6987	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9266	Approved
0.6985	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD74	Approved
0.6971	Remote Similarity	NPD8150	Discontinued
0.6959	Remote Similarity	NPD7472	Approved
0.6957	Remote Similarity	NPD3226	Approved
0.6951	Remote Similarity	NPD3817	Phase 2
0.695	Remote Similarity	NPD9493	Approved
0.6948	Remote Similarity	NPD1551	Phase 2
0.6944	Remote Similarity	NPD3026	Approved
0.6944	Remote Similarity	NPD3023	Approved
0.6936	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD3025	Approved
0.6923	Remote Similarity	NPD3024	Approved
0.6919	Remote Similarity	NPD5953	Discontinued
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9264	Approved
0.6912	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9263	Approved
0.6912	Remote Similarity	NPD9267	Approved
0.6903	Remote Similarity	NPD2346	Discontinued
0.6901	Remote Similarity	NPD7286	Phase 2
0.6894	Remote Similarity	NPD3020	Approved
0.6879	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD7251	Discontinued
0.6879	Remote Similarity	NPD4628	Phase 3
0.6851	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD9269	Phase 2
0.6842	Remote Similarity	NPD3818	Discontinued
0.6833	Remote Similarity	NPD4363	Phase 3
0.6833	Remote Similarity	NPD4360	Phase 2
0.6832	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5403	Approved
0.6832	Remote Similarity	NPD920	Approved
0.6824	Remote Similarity	NPD2797	Approved
0.6824	Remote Similarity	NPD1203	Approved
0.6821	Remote Similarity	NPD6797	Phase 2
0.6816	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD9268	Approved
0.6798	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1809	Phase 2
0.6792	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6663	Approved
0.6765	Remote Similarity	NPD3926	Phase 2
0.6748	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1930	Approved
0.6741	Remote Similarity	NPD1929	Approved
0.6741	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD9545	Approved
0.6735	Remote Similarity	NPD4878	Approved
0.6733	Remote Similarity	NPD5736	Approved
0.6724	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1242	Phase 1
0.6709	Remote Similarity	NPD2654	Approved
0.6708	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5401	Approved
0.6706	Remote Similarity	NPD5710	Approved
0.6706	Remote Similarity	NPD5711	Approved
0.6706	Remote Similarity	NPD7229	Phase 3
0.6705	Remote Similarity	NPD8313	Approved
0.6705	Remote Similarity	NPD8312	Approved
0.6704	Remote Similarity	NPD4287	Approved
0.6703	Remote Similarity	NPD4361	Phase 2
0.6703	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9281	Approved
0.6689	Remote Similarity	NPD6832	Phase 2
0.6688	Remote Similarity	NPD230	Phase 1
0.6687	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD1610	Phase 2
0.6648	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5402	Approved
0.6647	Remote Similarity	NPD2296	Approved
0.6647	Remote Similarity	NPD4288	Approved
0.6645	Remote Similarity	NPD7008	Discontinued
0.6644	Remote Similarity	NPD1876	Approved
0.6644	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD845	Approved
0.663	Remote Similarity	NPD7700	Phase 2
0.663	Remote Similarity	NPD7699	Phase 2
0.6622	Remote Similarity	NPD9717	Approved
0.6618	Remote Similarity	NPD9261	Approved
0.6601	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3267	Approved
0.66	Remote Similarity	NPD3266	Approved
0.6596	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD8434	Phase 2
0.6591	Remote Similarity	NPD2933	Approved
0.6591	Remote Similarity	NPD2934	Approved
0.6591	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1465	Phase 2
0.6582	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5124	Phase 1
0.6577	Remote Similarity	NPD1755	Approved
0.6571	Remote Similarity	NPD3021	Approved
0.6571	Remote Similarity	NPD3022	Approved
0.6566	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6273	Approved
0.6561	Remote Similarity	NPD4308	Phase 3
0.6559	Remote Similarity	NPD7501	Clinical (unspecified phase)

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