NPASS Compound

Structure

NPC470986 OpenBabel07101718292D 38 40 0 0 1 0 0 0 0 0999 V2000 1.6898 2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7592 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6041 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -6.3415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -4.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9143 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0694 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7592 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -5.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -4.8780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5347 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -4.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -4.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -6.3415 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0694 -4.8780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -4.8780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 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 7 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 21 1 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 20 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 18 32 2 0 0 0 0 19 24 1 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 22 2 0 0 0 0 21 38 1 0 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 30 2 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 28 2 0 0 0 0 25 30 1 0 0 0 0 26 29 2 0 0 0 0 26 31 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 37 2 0 0 0 0 31 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.18
Volume:	429.691
LogP:	4.809
LogD:	2.073
LogS:	-3.553
# Rotatable Bonds:	7
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	3.271
Fsp3:	0.391
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:	-5.036
MDCK Permeability:	1.2584621799760498e-05
Pgp-inhibitor:	0.779
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.206
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	98.15557098388672%
Volume Distribution (VD):	0.46
Pgp-substrate:	2.3475186824798584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.248
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.207
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.676
CYP2D6-inhibitor:	0.159
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	3.485
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.923
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.159
Respiratory Toxicity:	0.182

Download Data

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

Natural Product: NPC470986

Natural Product ID:	NPC470986
*Common Name:**	3-[[3-Acetyl-2,4,6-Trihydroxy-5-(3-Methylbut-2-Enyl)Phenyl]-Phenylmethyl]-4-Hydroxy-5-Propan-2-Yl-6-Propylpyran-2-One
IUPAC Name:	3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]-phenylmethyl]-4-hydroxy-5-propan-2-yl-6-propylpyran-2-one
Synonyms:
Standard InCHIKey:	OIBBWFLGWHQBFZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C31H36O7/c1-7-11-21-22(17(4)5)29(35)26(31(37)38-21)24(19-12-9-8-10-13-19)25-28(34)20(15-14-16(2)3)27(33)23(18(6)32)30(25)36/h8-10,12-14,17,24,33-36H,7,11,15H2,1-6H3
SMILES:	CCCc1oc(=O)c(c(c1C(C)C)O)C(c1c(O)c(CC=C(C)C)c(c(c1O)C(=O)C)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334818
PubChem CID:	71716407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO25148.1	Helichrysum italicum	Under-species	n.a.	n.a.	Flowered aerial parts	Arzana, Sardinia	2010-Jul	PMID[23265253]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[453923]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.0	ug.mL-1	PMID[453923]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[453923]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[453923]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[453923]

☑ 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 NPC470986 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	371
0.1-0.2	1567
0.2-0.3	3682
0.3-0.4	9087
0.4-0.5	9717
0.5-0.6	3826
0.6-0.7	6083
0.7-0.8	4996
0.8-0.85	1989
0.85-0.9	1167
0.9-0.95	168
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
0.9549	High Similarity	NPC470984
0.9474	High Similarity	NPC470988
0.9429	High Similarity	NPC181388
0.9398	High Similarity	NPC185624
0.9357	High Similarity	NPC178627
0.9357	High Similarity	NPC469935
0.9357	High Similarity	NPC196137
0.9357	High Similarity	NPC1886
0.9338	High Similarity	NPC470985
0.9338	High Similarity	NPC470989
0.9291	High Similarity	NPC470322
0.9291	High Similarity	NPC154217
0.9286	High Similarity	NPC94794
0.9286	High Similarity	NPC470296
0.9286	High Similarity	NPC112791
0.9286	High Similarity	NPC196459
0.9286	High Similarity	NPC188632
0.9286	High Similarity	NPC87609
0.9248	High Similarity	NPC470987
0.9248	High Similarity	NPC21378
0.9231	High Similarity	NPC469932
0.9214	High Similarity	NPC36181
0.9161	High Similarity	NPC469933
0.9161	High Similarity	NPC161864
0.9161	High Similarity	NPC208303
0.9155	High Similarity	NPC25844
0.9091	High Similarity	NPC249942
0.9091	High Similarity	NPC297886
0.9091	High Similarity	NPC140120
0.9085	High Similarity	NPC469953
0.9078	High Similarity	NPC297600
0.9065	High Similarity	NPC112789
0.9065	High Similarity	NPC19622
0.9048	High Similarity	NPC469934
0.9034	High Similarity	NPC474735
0.9021	High Similarity	NPC57470
0.9014	High Similarity	NPC11700
0.9007	High Similarity	NPC282300
0.9	High Similarity	NPC301217
0.9	High Similarity	NPC19476
0.9	High Similarity	NPC217186
0.9	High Similarity	NPC303633
0.9	High Similarity	NPC283429
0.9	High Similarity	NPC275903
0.9	High Similarity	NPC241975
0.9	High Similarity	NPC53181
0.9	High Similarity	NPC220062
0.9	High Similarity	NPC55018
0.9	High Similarity	NPC216978
0.9	High Similarity	NPC96565
0.9	High Similarity	NPC473209
0.8978	High Similarity	NPC475088
0.8973	High Similarity	NPC290671
0.8973	High Similarity	NPC209142
0.8973	High Similarity	NPC312549
0.8966	High Similarity	NPC19238
0.8966	High Similarity	NPC164205
0.8966	High Similarity	NPC104236
0.8958	High Similarity	NPC180477
0.8951	High Similarity	NPC326500
0.8951	High Similarity	NPC271288
0.8936	High Similarity	NPC48624
0.8936	High Similarity	NPC204985
0.8936	High Similarity	NPC261227
0.8936	High Similarity	NPC215311
0.8936	High Similarity	NPC172250
0.8936	High Similarity	NPC159275
0.8936	High Similarity	NPC213659
0.8936	High Similarity	NPC265178
0.8936	High Similarity	NPC259166
0.8936	High Similarity	NPC270883
0.8936	High Similarity	NPC326109
0.8936	High Similarity	NPC144118
0.8936	High Similarity	NPC80962
0.8936	High Similarity	NPC172986
0.8936	High Similarity	NPC241100
0.8936	High Similarity	NPC219917
0.8929	High Similarity	NPC183639
0.8929	High Similarity	NPC201395
0.8929	High Similarity	NPC199458
0.8929	High Similarity	NPC470083
0.8929	High Similarity	NPC219584
0.8913	High Similarity	NPC103842
0.8897	High Similarity	NPC145467
0.8889	High Similarity	NPC477955
0.8881	High Similarity	NPC219915
0.8881	High Similarity	NPC24821
0.8881	High Similarity	NPC190637
0.8881	High Similarity	NPC212932
0.8881	High Similarity	NPC116513
0.8881	High Similarity	NPC9117
0.8881	High Similarity	NPC293053
0.8873	High Similarity	NPC268204
0.8873	High Similarity	NPC470555
0.8873	High Similarity	NPC232021
0.8873	High Similarity	NPC40118
0.8873	High Similarity	NPC469404
0.8873	High Similarity	NPC26051
0.8873	High Similarity	NPC110969
0.8873	High Similarity	NPC126534
0.8873	High Similarity	NPC52789
0.8873	High Similarity	NPC55832
0.8873	High Similarity	NPC205006
0.8873	High Similarity	NPC156590
0.8873	High Similarity	NPC118840
0.8873	High Similarity	NPC147688
0.8873	High Similarity	NPC64908
0.8865	High Similarity	NPC18260
0.8865	High Similarity	NPC78913
0.8865	High Similarity	NPC472343
0.8865	High Similarity	NPC295384
0.8865	High Similarity	NPC477956
0.8857	High Similarity	NPC474624
0.8857	High Similarity	NPC153979
0.8857	High Similarity	NPC255801
0.8857	High Similarity	NPC138047
0.8857	High Similarity	NPC322301
0.8857	High Similarity	NPC131782
0.8849	High Similarity	NPC13575
0.8849	High Similarity	NPC50455
0.8849	High Similarity	NPC156092
0.8844	High Similarity	NPC316960
0.8844	High Similarity	NPC204561
0.8844	High Similarity	NPC78835
0.8844	High Similarity	NPC317715
0.8844	High Similarity	NPC309512
0.8844	High Similarity	NPC148945
0.8832	High Similarity	NPC175738
0.8828	High Similarity	NPC308200
0.8828	High Similarity	NPC475348
0.8828	High Similarity	NPC125801
0.8828	High Similarity	NPC261271
0.8819	High Similarity	NPC235217
0.8819	High Similarity	NPC473014
0.8819	High Similarity	NPC311741
0.8819	High Similarity	NPC216538
0.8819	High Similarity	NPC234629
0.8819	High Similarity	NPC476055
0.8819	High Similarity	NPC273538
0.8815	High Similarity	NPC473017
0.8811	High Similarity	NPC293852
0.8811	High Similarity	NPC217083
0.8811	High Similarity	NPC266725
0.8811	High Similarity	NPC299080
0.8811	High Similarity	NPC11561
0.8811	High Similarity	NPC226636
0.8811	High Similarity	NPC144499
0.8811	High Similarity	NPC78803
0.8811	High Similarity	NPC214236
0.8811	High Similarity	NPC59739
0.8811	High Similarity	NPC200694
0.8811	High Similarity	NPC473042
0.8811	High Similarity	NPC62840
0.8806	High Similarity	NPC267846
0.8803	High Similarity	NPC101366
0.8803	High Similarity	NPC11056
0.8803	High Similarity	NPC69769
0.8803	High Similarity	NPC221173
0.8803	High Similarity	NPC475680
0.8803	High Similarity	NPC305355
0.8803	High Similarity	NPC477272
0.8803	High Similarity	NPC235239
0.8803	High Similarity	NPC253822
0.8803	High Similarity	NPC150522
0.8794	High Similarity	NPC470669
0.8794	High Similarity	NPC21350
0.8794	High Similarity	NPC243528
0.8794	High Similarity	NPC470668
0.8794	High Similarity	NPC251681
0.8786	High Similarity	NPC41461
0.8786	High Similarity	NPC168105
0.8786	High Similarity	NPC25287
0.8786	High Similarity	NPC213603
0.8786	High Similarity	NPC24394
0.8786	High Similarity	NPC249606
0.8786	High Similarity	NPC477242
0.8786	High Similarity	NPC13408
0.8786	High Similarity	NPC12165
0.8786	High Similarity	NPC194579
0.8786	High Similarity	NPC98115
0.8786	High Similarity	NPC186838
0.8786	High Similarity	NPC477244
0.8786	High Similarity	NPC150399
0.8786	High Similarity	NPC1486
0.8786	High Similarity	NPC477243
0.8786	High Similarity	NPC274109
0.8786	High Similarity	NPC66349
0.8776	High Similarity	NPC158866
0.8776	High Similarity	NPC29777
0.8776	High Similarity	NPC471115
0.8776	High Similarity	NPC151973
0.8767	High Similarity	NPC39195
0.8767	High Similarity	NPC152233
0.8759	High Similarity	NPC124729
0.8759	High Similarity	NPC225173
0.8759	High Similarity	NPC474161
0.8759	High Similarity	NPC285630
0.8759	High Similarity	NPC178343
0.8759	High Similarity	NPC127059
0.8759	High Similarity	NPC163846

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 NPC470986 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	947
0.2-0.3	1511
0.3-0.4	2575
0.4-0.5	2034
0.5-0.6	1183
0.6-0.7	373
0.7-0.8	130
0.8-0.85	40
0.85-0.9	17
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8819	High Similarity	NPD4378	Clinical (unspecified phase)
0.869	High Similarity	NPD7410	Clinical (unspecified phase)
0.86	High Similarity	NPD7819	Suspended
0.8582	High Similarity	NPD1510	Phase 2
0.8553	High Similarity	NPD7075	Discontinued
0.8543	High Similarity	NPD8443	Clinical (unspecified phase)
0.8531	High Similarity	NPD970	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD7411	Suspended
0.8429	Intermediate Similarity	NPD1240	Approved
0.8414	Intermediate Similarity	NPD3750	Approved
0.84	Intermediate Similarity	NPD4380	Phase 2
0.8366	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1607	Approved
0.8291	Intermediate Similarity	NPD7473	Discontinued
0.8289	Intermediate Similarity	NPD6801	Discontinued
0.8276	Intermediate Similarity	NPD1549	Phase 2
0.8264	Intermediate Similarity	NPD2796	Approved
0.8235	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2799	Discontinued
0.8194	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2532	Approved
0.8188	Intermediate Similarity	NPD2534	Approved
0.8188	Intermediate Similarity	NPD2533	Approved
0.8182	Intermediate Similarity	NPD6651	Approved
0.8138	Intermediate Similarity	NPD2935	Discontinued
0.8121	Intermediate Similarity	NPD6799	Approved
0.8121	Intermediate Similarity	NPD1511	Approved
0.8101	Intermediate Similarity	NPD6232	Discontinued
0.8095	Intermediate Similarity	NPD2800	Approved
0.8095	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1243	Approved
0.8077	Intermediate Similarity	NPD3749	Approved
0.8069	Intermediate Similarity	NPD3748	Approved
0.8039	Intermediate Similarity	NPD6599	Discontinued
0.8028	Intermediate Similarity	NPD2313	Discontinued
0.8028	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD5405	Approved
0.8014	Intermediate Similarity	NPD5404	Approved
0.8014	Intermediate Similarity	NPD5408	Approved
0.8014	Intermediate Similarity	NPD5406	Approved
0.8013	Intermediate Similarity	NPD1512	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.8	Intermediate Similarity	NPD7390	Discontinued
0.7963	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3817	Phase 2
0.7935	Intermediate Similarity	NPD1934	Approved
0.7929	Intermediate Similarity	NPD1164	Approved
0.7919	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD943	Approved
0.7902	Intermediate Similarity	NPD3268	Approved
0.7891	Intermediate Similarity	NPD1551	Phase 2
0.7872	Intermediate Similarity	NPD2798	Approved
0.7843	Intermediate Similarity	NPD920	Approved
0.7815	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6959	Discontinued
0.7801	Intermediate Similarity	NPD2797	Approved
0.78	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3764	Approved
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD5953	Discontinued
0.7744	Intermediate Similarity	NPD7286	Phase 2
0.7742	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD5403	Approved
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7712	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1203	Approved
0.7673	Intermediate Similarity	NPD3882	Suspended
0.7651	Intermediate Similarity	NPD6100	Approved
0.7651	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD1201	Approved
0.764	Intermediate Similarity	NPD5494	Approved
0.7636	Intermediate Similarity	NPD7054	Approved
0.7628	Intermediate Similarity	NPD7458	Discontinued
0.7609	Intermediate Similarity	NPD9545	Approved
0.76	Intermediate Similarity	NPD2344	Approved
0.7597	Intermediate Similarity	NPD5401	Approved
0.7591	Intermediate Similarity	NPD9493	Approved
0.759	Intermediate Similarity	NPD7472	Approved
0.759	Intermediate Similarity	NPD7074	Phase 3
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7566	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6166	Phase 2
0.7552	Intermediate Similarity	NPD3266	Approved
0.7552	Intermediate Similarity	NPD3267	Approved
0.7552	Intermediate Similarity	NPD1470	Approved
0.7546	Intermediate Similarity	NPD5710	Approved
0.7546	Intermediate Similarity	NPD5711	Approved
0.7534	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7518	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD230	Phase 1
0.7469	Intermediate Similarity	NPD919	Approved
0.7467	Intermediate Similarity	NPD4308	Phase 3
0.7467	Intermediate Similarity	NPD7033	Discontinued
0.7465	Intermediate Similarity	NPD1608	Approved
0.7465	Intermediate Similarity	NPD9717	Approved
0.7456	Intermediate Similarity	NPD7808	Phase 3
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7003	Approved
0.744	Intermediate Similarity	NPD6797	Phase 2
0.7429	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2309	Approved
0.7397	Intermediate Similarity	NPD4908	Phase 1
0.7391	Intermediate Similarity	NPD4288	Approved
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3225	Approved
0.7351	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.733	Intermediate Similarity	NPD4363	Phase 3
0.733	Intermediate Similarity	NPD4360	Phase 2
0.7329	Intermediate Similarity	NPD1465	Phase 2
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4361	Phase 2
0.7288	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9266	Approved
0.7259	Intermediate Similarity	NPD74	Approved
0.7255	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD17	Approved
0.7218	Intermediate Similarity	NPD5909	Discontinued
0.72	Intermediate Similarity	NPD4287	Approved
0.72	Intermediate Similarity	NPD4307	Phase 2
0.7197	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9267	Approved
0.7185	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9263	Approved
0.7185	Intermediate Similarity	NPD9264	Approved
0.7181	Intermediate Similarity	NPD1296	Phase 2
0.7161	Intermediate Similarity	NPD2654	Approved
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7143	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1283	Approved
0.7115	Intermediate Similarity	NPD8166	Discontinued
0.7114	Intermediate Similarity	NPD4625	Phase 3
0.7113	Intermediate Similarity	NPD1548	Phase 1
0.711	Intermediate Similarity	NPD8312	Approved
0.711	Intermediate Similarity	NPD8313	Approved
0.7103	Intermediate Similarity	NPD9269	Phase 2
0.7103	Intermediate Similarity	NPD3972	Approved
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5890	Approved
0.7099	Intermediate Similarity	NPD5889	Approved
0.7083	Intermediate Similarity	NPD3926	Phase 2
0.7073	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6190	Approved
0.7067	Intermediate Similarity	NPD411	Approved
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7066	Intermediate Similarity	NPD1247	Approved
0.7063	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD37	Approved
0.7048	Intermediate Similarity	NPD6234	Discontinued
0.7039	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD447	Suspended
0.7039	Intermediate Similarity	NPD1933	Approved
0.7034	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6002	Phase 3
0.7032	Intermediate Similarity	NPD6005	Phase 3
0.7032	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6004	Phase 3
0.703	Intermediate Similarity	NPD4966	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.703	Intermediate Similarity	NPD4965	Approved
0.7018	Intermediate Similarity	NPD6020	Phase 2
0.7015	Intermediate Similarity	NPD1929	Approved
0.7015	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1930	Approved
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6989	Remote Similarity	NPD8434	Phase 2
0.6982	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4060	Phase 1
0.6972	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4477	Approved
0.6968	Remote Similarity	NPD4476	Approved
0.6954	Remote Similarity	NPD6798	Discontinued
0.695	Remote Similarity	NPD9281	Approved
0.695	Remote Similarity	NPD5951	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