NPASS Compound

Structure

NPC121568 OpenBabel07101719132D 43 47 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 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 5.1962 -0.0000 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 6.9282 -0.0000 0.0000 C 0 0 0 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 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 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 6.0622 -0.5000 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 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 2 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 -1.7321 0.0000 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 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -2.5981 -0.5000 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 23 1 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 24 2 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 26 2 0 0 0 0 20 33 1 0 0 0 0 21 28 1 0 0 0 0 21 32 1 0 0 0 0 22 30 2 0 0 0 0 22 31 1 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 27 28 1 0 0 0 0 27 33 2 0 0 0 0 28 34 1 6 0 0 0 29 35 1 0 0 0 0 29 39 2 0 0 0 0 30 34 1 0 0 0 0 30 40 1 0 0 0 0 31 35 2 0 0 0 0 31 41 1 0 0 0 0 32 24 1 1 0 0 0 32 43 1 0 0 0 0 33 43 1 0 0 0 0 34 36 2 0 0 0 0 35 36 1 0 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.26
Volume:	615.687
LogP:	7.89
LogD:	4.471
LogS:	-3.104
# Rotatable Bonds:	12
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.085
Synthetic Accessibility Score:	3.633
Fsp3:	0.306
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.411
MDCK Permeability:	1.7107280655181967e-05
Pgp-inhibitor:	0.192
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	101.56365203857422%
Volume Distribution (VD):	0.487
Pgp-substrate:	0.5127279758453369%

ADMET: Metabolism

CYP1A2-inhibitor:	0.199
CYP1A2-substrate:	0.549
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	5.973
Half-life (T1/2):	0.398

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.542
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.955
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.894
Respiratory Toxicity:	0.437

Download Data

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

Natural Product: NPC121568

Natural Product ID:	NPC121568
*Common Name:**	(+)-Myristinin D
IUPAC Name:	9-phenyl-1-[2,4,6-trihydroxy-3-[(2S,4R)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]phenyl]nonan-1-one
Synonyms:	(+)-Myristinin D
Standard InCHIKey:	NWJOIWGNEIDTTG-NSJVFKKDSA-N
Standard InCHI:	InChI=1S/C36H38O7/c37-25-16-14-24(15-17-25)32-21-28(27-19-18-26(38)20-33(27)43-32)34-30(40)22-31(41)35(36(34)42)29(39)13-9-4-2-1-3-6-10-23-11-7-5-8-12-23/h5,7-8,11-12,14-20,22,28,32,37-38,40-42H,1-4,6,9-10,13,21H2/t28-,32+/m1/s1
SMILES:	Oc1ccc2c(c1)O[C@@H](C[C@H]2c1c(O)cc(c(c1O)C(=O)CCCCCCCCc1ccccc1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448072
PubChem CID:	497362
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002991] Hydroxyflavonoids [CHEMONTID:0002993] 7-hydroxyflavonoids

*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
NPO6742	Knema elegans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309311]
NPO6742	Knema elegans	Species	Myristicaceae	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	2
Ki	1
Others	3

Activity Type	# Activity
Individual Protein	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	4300.0	nM	PMID[553308]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	1200.0	nM	PMID[553308]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Ki	=	12000.0	nM	PMID[553308]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Kis	=	23.0	uM	PMID[553308]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Kii	=	0.8	uM	PMID[553308]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	30.0	%	PMID[553308]

☑ 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 NPC121568 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	415
0.1-0.2	1589
0.2-0.3	3703
0.3-0.4	9380
0.4-0.5	9202
0.5-0.6	3700
0.6-0.7	5904
0.7-0.8	5348
0.8-0.85	2088
0.85-0.9	967
0.9-0.95	342
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC1796
0.9799	High Similarity	NPC257166
0.9733	High Similarity	NPC15815
0.9733	High Similarity	NPC51247
0.9728	High Similarity	NPC178484
0.9669	High Similarity	NPC226462
0.9669	High Similarity	NPC98023
0.9669	High Similarity	NPC195136
0.9669	High Similarity	NPC42965
0.9667	High Similarity	NPC322459
0.9667	High Similarity	NPC318527
0.9667	High Similarity	NPC324358
0.9667	High Similarity	NPC323627
0.9664	High Similarity	NPC79375
0.9664	High Similarity	NPC37253
0.9662	High Similarity	NPC39154
0.9662	High Similarity	NPC208011
0.9662	High Similarity	NPC78324
0.9662	High Similarity	NPC115601
0.9658	High Similarity	NPC122894
0.9603	High Similarity	NPC105584
0.96	High Similarity	NPC32867
0.96	High Similarity	NPC69531
0.9592	High Similarity	NPC3642
0.9592	High Similarity	NPC132345
0.9542	High Similarity	NPC473012
0.9539	High Similarity	NPC121647
0.9536	High Similarity	NPC475184
0.9536	High Similarity	NPC208258
0.9533	High Similarity	NPC134171
0.9533	High Similarity	NPC66441
0.9533	High Similarity	NPC300668
0.9533	High Similarity	NPC182555
0.953	High Similarity	NPC174086
0.9481	High Similarity	NPC473009
0.9477	High Similarity	NPC312273
0.9477	High Similarity	NPC301256
0.9474	High Similarity	NPC295090
0.9463	High Similarity	NPC476551
0.9463	High Similarity	NPC78835
0.9463	High Similarity	NPC317715
0.9463	High Similarity	NPC476553
0.9463	High Similarity	NPC309512
0.9463	High Similarity	NPC148945
0.9463	High Similarity	NPC316960
0.9463	High Similarity	NPC204561
0.9463	High Similarity	NPC476552
0.9456	High Similarity	NPC261271
0.9456	High Similarity	NPC475348
0.9452	High Similarity	NPC470135
0.9452	High Similarity	NPC470136
0.9452	High Similarity	NPC39045
0.9419	High Similarity	NPC473010
0.9408	High Similarity	NPC287789
0.9408	High Similarity	NPC271741
0.9404	High Similarity	NPC201227
0.9404	High Similarity	NPC258474
0.94	High Similarity	NPC43345
0.9392	High Similarity	NPC152233
0.9388	High Similarity	NPC470132
0.9388	High Similarity	NPC470134
0.9388	High Similarity	NPC470131
0.9388	High Similarity	NPC470133
0.9388	High Similarity	NPC109183
0.9388	High Similarity	NPC473078
0.9359	High Similarity	NPC251336
0.9346	High Similarity	NPC195167
0.9346	High Similarity	NPC51760
0.9342	High Similarity	NPC56049
0.9342	High Similarity	NPC309648
0.9342	High Similarity	NPC61112
0.9342	High Similarity	NPC198489
0.9342	High Similarity	NPC54830
0.9338	High Similarity	NPC324447
0.9329	High Similarity	NPC473016
0.932	High Similarity	NPC271288
0.932	High Similarity	NPC473014
0.932	High Similarity	NPC235217
0.929	High Similarity	NPC473011
0.9286	High Similarity	NPC184326
0.9286	High Similarity	NPC292863
0.9276	High Similarity	NPC121649
0.9276	High Similarity	NPC205026
0.9276	High Similarity	NPC248739
0.9276	High Similarity	NPC14606
0.9276	High Similarity	NPC150908
0.9276	High Similarity	NPC186227
0.9276	High Similarity	NPC158027
0.9276	High Similarity	NPC215203
0.9276	High Similarity	NPC52611
0.9276	High Similarity	NPC100049
0.9276	High Similarity	NPC265624
0.9276	High Similarity	NPC159707
0.9262	High Similarity	NPC145467
0.9257	High Similarity	NPC228779
0.9257	High Similarity	NPC285630
0.9257	High Similarity	NPC127059
0.9252	High Similarity	NPC107177
0.9252	High Similarity	NPC223812
0.9252	High Similarity	NPC85162
0.9252	High Similarity	NPC185276
0.9252	High Similarity	NPC81697
0.9252	High Similarity	NPC77794
0.9252	High Similarity	NPC278249
0.9252	High Similarity	NPC125894
0.9231	High Similarity	NPC63438
0.9226	High Similarity	NPC137232
0.9226	High Similarity	NPC114652
0.9226	High Similarity	NPC18380
0.9226	High Similarity	NPC175513
0.9221	High Similarity	NPC123544
0.9211	High Similarity	NPC72425
0.9211	High Similarity	NPC303485
0.9211	High Similarity	NPC194593
0.9211	High Similarity	NPC71061
0.9211	High Similarity	NPC290830
0.9205	High Similarity	NPC111112
0.9205	High Similarity	NPC138299
0.9205	High Similarity	NPC222713
0.9205	High Similarity	NPC67322
0.92	High Similarity	NPC288840
0.92	High Similarity	NPC291746
0.9195	High Similarity	NPC283234
0.9195	High Similarity	NPC296998
0.9195	High Similarity	NPC10990
0.9195	High Similarity	NPC473077
0.9195	High Similarity	NPC300988
0.9195	High Similarity	NPC308200
0.9189	High Similarity	NPC236766
0.9189	High Similarity	NPC194949
0.9189	High Similarity	NPC473015
0.9189	High Similarity	NPC131568
0.9189	High Similarity	NPC131579
0.9189	High Similarity	NPC282957
0.9189	High Similarity	NPC473013
0.9189	High Similarity	NPC471473
0.9189	High Similarity	NPC471524
0.9189	High Similarity	NPC471523
0.9189	High Similarity	NPC197252
0.9184	High Similarity	NPC32739
0.9184	High Similarity	NPC265040
0.9184	High Similarity	NPC227579
0.9184	High Similarity	NPC223500
0.9184	High Similarity	NPC328164
0.9184	High Similarity	NPC78
0.9184	High Similarity	NPC10937
0.9184	High Similarity	NPC220998
0.9184	High Similarity	NPC166482
0.9184	High Similarity	NPC66515
0.9184	High Similarity	NPC296917
0.9184	High Similarity	NPC324436
0.9184	High Similarity	NPC306829
0.9184	High Similarity	NPC324134
0.9184	High Similarity	NPC40833
0.9184	High Similarity	NPC228504
0.9184	High Similarity	NPC76372
0.9184	High Similarity	NPC125855
0.9184	High Similarity	NPC182852
0.9184	High Similarity	NPC161506
0.9184	High Similarity	NPC107572
0.9184	High Similarity	NPC37496
0.9184	High Similarity	NPC166934
0.9184	High Similarity	NPC194432
0.9184	High Similarity	NPC148757
0.9184	High Similarity	NPC76338
0.9184	High Similarity	NPC177354
0.9184	High Similarity	NPC1089
0.9184	High Similarity	NPC167624
0.9184	High Similarity	NPC64915
0.9161	High Similarity	NPC114147
0.9139	High Similarity	NPC29777
0.9139	High Similarity	NPC471115
0.9133	High Similarity	NPC132592
0.9133	High Similarity	NPC35150
0.9133	High Similarity	NPC161191
0.9133	High Similarity	NPC39195
0.9133	High Similarity	NPC160821
0.9133	High Similarity	NPC106328
0.9128	High Similarity	NPC301276
0.9128	High Similarity	NPC214774
0.9128	High Similarity	NPC20488
0.9128	High Similarity	NPC312973
0.9128	High Similarity	NPC83357
0.9128	High Similarity	NPC475052
0.9128	High Similarity	NPC267375
0.9128	High Similarity	NPC54577
0.9128	High Similarity	NPC246948
0.9128	High Similarity	NPC142405
0.9128	High Similarity	NPC470647
0.9128	High Similarity	NPC476088
0.9128	High Similarity	NPC195621
0.9128	High Similarity	NPC67805
0.9128	High Similarity	NPC176229
0.9128	High Similarity	NPC472629
0.9128	High Similarity	NPC477955
0.9128	High Similarity	NPC88964
0.9128	High Similarity	NPC474161
0.9128	High Similarity	NPC111786
0.9125	High Similarity	NPC477529
0.9122	High Similarity	NPC68104

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 NPC121568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	963
0.2-0.3	1480
0.3-0.4	2631
0.4-0.5	1910
0.5-0.6	1168
0.6-0.7	424
0.7-0.8	149
0.8-0.85	31
0.85-0.9	13
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9533	High Similarity	NPD8443	Clinical (unspecified phase)
0.9051	High Similarity	NPD7852	Clinical (unspecified phase)
0.8981	High Similarity	NPD6959	Discontinued
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8968	High Similarity	NPD7768	Phase 2
0.8912	High Similarity	NPD1549	Phase 2
0.8831	High Similarity	NPD7411	Suspended
0.8808	High Similarity	NPD7410	Clinical (unspecified phase)
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.8766	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD2393	Clinical (unspecified phase)
0.8718	High Similarity	NPD7819	Suspended
0.8671	High Similarity	NPD7075	Discontinued
0.8599	High Similarity	NPD7096	Clinical (unspecified phase)
0.8581	High Similarity	NPD1510	Phase 2
0.8537	High Similarity	NPD7804	Clinical (unspecified phase)
0.8523	High Similarity	NPD2796	Approved
0.8466	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6166	Phase 2
0.8438	Intermediate Similarity	NPD3749	Approved
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD1934	Approved
0.8311	Intermediate Similarity	NPD1240	Approved
0.8299	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5494	Approved
0.82	Intermediate Similarity	NPD1607	Approved
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD3750	Approved
0.8163	Intermediate Similarity	NPD4908	Phase 1
0.8155	Intermediate Similarity	NPD7074	Phase 3
0.8148	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1511	Approved
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7054	Approved
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.807	Intermediate Similarity	NPD8312	Approved
0.807	Intermediate Similarity	NPD8313	Approved
0.8047	Intermediate Similarity	NPD7472	Approved
0.8038	Intermediate Similarity	NPD1512	Approved
0.8025	Intermediate Similarity	NPD7390	Discontinued
0.8025	Intermediate Similarity	NPD2801	Approved
0.8025	Intermediate Similarity	NPD6799	Approved
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD2800	Approved
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7961	Intermediate Similarity	NPD6651	Approved
0.7953	Intermediate Similarity	NPD7251	Discontinued
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3882	Suspended
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7914	Intermediate Similarity	NPD8455	Phase 2
0.7907	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7895	Intermediate Similarity	NPD6797	Phase 2
0.7875	Intermediate Similarity	NPD5403	Approved
0.7862	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3748	Approved
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7824	Intermediate Similarity	NPD3818	Discontinued
0.7808	Intermediate Similarity	NPD1610	Phase 2
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD6099	Approved
0.7778	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7458	Discontinued
0.7765	Intermediate Similarity	NPD4360	Phase 2
0.7765	Intermediate Similarity	NPD4363	Phase 3
0.7758	Intermediate Similarity	NPD3817	Phase 2
0.7756	Intermediate Similarity	NPD2344	Approved
0.7753	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5401	Approved
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7688	Intermediate Similarity	NPD5953	Discontinued
0.7687	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7286	Phase 2
0.7658	Intermediate Similarity	NPD1243	Approved
0.7654	Intermediate Similarity	NPD920	Approved
0.7651	Intermediate Similarity	NPD5402	Approved
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7003	Approved
0.761	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD5406	Approved
0.758	Intermediate Similarity	NPD5408	Approved
0.758	Intermediate Similarity	NPD5405	Approved
0.758	Intermediate Similarity	NPD5404	Approved
0.7576	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2309	Approved
0.7561	Intermediate Similarity	NPD3226	Approved
0.7548	Intermediate Similarity	NPD5124	Phase 1
0.7548	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7444	Intermediate Similarity	NPD4287	Approved
0.7434	Intermediate Similarity	NPD2798	Approved
0.7432	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4361	Phase 2
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7381	Intermediate Similarity	NPD1465	Phase 2
0.7372	Intermediate Similarity	NPD943	Approved
0.7368	Intermediate Similarity	NPD2797	Approved
0.7341	Intermediate Similarity	NPD3926	Phase 2
0.734	Intermediate Similarity	NPD7697	Approved
0.734	Intermediate Similarity	NPD7696	Phase 3
0.734	Intermediate Similarity	NPD7698	Approved
0.7333	Intermediate Similarity	NPD8150	Discontinued
0.7321	Intermediate Similarity	NPD7577	Discontinued
0.7317	Intermediate Similarity	NPD7447	Phase 1
0.7314	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7177	Discontinued
0.731	Intermediate Similarity	NPD919	Approved
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7213	Phase 3
0.7256	Intermediate Similarity	NPD7212	Phase 2
0.7254	Intermediate Similarity	NPD7783	Phase 2
0.7254	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7435	Discontinued
0.7244	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3764	Approved
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7235	Intermediate Similarity	NPD4288	Approved
0.7229	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7225	Intermediate Similarity	NPD1247	Approved
0.7225	Intermediate Similarity	NPD7584	Approved
0.7219	Intermediate Similarity	NPD1201	Approved
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3225	Approved
0.7188	Intermediate Similarity	NPD7701	Phase 2
0.7182	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5761	Phase 2
0.7176	Intermediate Similarity	NPD5760	Phase 2
0.7171	Intermediate Similarity	NPD1608	Approved
0.7171	Intermediate Similarity	NPD9717	Approved
0.7165	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1729	Discontinued
0.7126	Intermediate Similarity	NPD7427	Discontinued
0.7125	Intermediate Similarity	NPD7097	Phase 1
0.7124	Intermediate Similarity	NPD4749	Approved
0.7119	Intermediate Similarity	NPD7228	Approved
0.7118	Intermediate Similarity	NPD6844	Discontinued
0.7117	Intermediate Similarity	NPD2654	Approved
0.7115	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7874	Approved
0.7105	Intermediate Similarity	NPD422	Phase 1
0.7105	Intermediate Similarity	NPD6823	Phase 2
0.7102	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7074	Intermediate Similarity	NPD7699	Phase 2
0.7074	Intermediate Similarity	NPD7700	Phase 2
0.7059	Intermediate Similarity	NPD5890	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7059	Intermediate Similarity	NPD5889	Approved
0.7056	Intermediate Similarity	NPD6104	Discontinued

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