NPASS Compound

Structure

NPC178484 OpenBabel07101719252D 40 43 0 0 1 0 0 0 0 0999 V2000 -2.5981 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -3.4641 -0.0000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -0.8660 -2.5000 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 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 -2.5981 -1.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 21 2 0 0 0 0 13 15 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 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 23 2 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 22 34 1 0 0 0 0 23 35 1 0 0 0 0 24 25 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 1 0 0 0 26 32 1 0 0 0 0 26 36 2 0 0 0 0 27 31 1 0 0 0 0 27 37 1 0 0 0 0 28 32 2 0 0 0 0 28 38 1 0 0 0 0 29 21 1 6 0 0 0 29 40 1 0 0 0 0 30 40 1 0 0 0 0 31 33 2 0 0 0 0 32 33 1 0 0 0 0 33 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.28
Volume:	580.265
LogP:	8.265
LogD:	4.611
LogS:	-3.155
# Rotatable Bonds:	13
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	3.654
Fsp3:	0.424
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.102
MDCK Permeability:	1.933047315105796e-05
Pgp-inhibitor:	0.137
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	101.17729949951172%
Volume Distribution (VD):	0.738
Pgp-substrate:	0.600141704082489%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.654
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.759
CYP2D6-substrate:	0.819
CYP3A4-inhibitor:	0.344
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	5.358
Half-life (T1/2):	0.357

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.529
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.956
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.901
Respiratory Toxicity:	0.567

Download Data

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

Natural Product: NPC178484

Natural Product ID:	NPC178484
*Common Name:**	(+)-Myristinin A
IUPAC Name:	1-[2,4,6-trihydroxy-3-[(2S,4R)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]phenyl]dodecan-1-one
Synonyms:	(+)-Myristinin A
Standard InCHIKey:	JGXZVDAPLSTBGZ-IRPSRAIASA-N
Standard InCHI:	InChI=1S/C33H40O7/c1-2-3-4-5-6-7-8-9-10-11-26(36)32-28(38)20-27(37)31(33(32)39)25-19-29(21-12-14-22(34)15-13-21)40-30-18-23(35)16-17-24(25)30/h12-18,20,25,29,34-35,37-39H,2-11,19H2,1H3/t25-,29+/m1/s1
SMILES:	CCCCCCCCCCCC(=O)c1c(cc(c([C@@H]2C[C@@H](c3ccc(cc3)O)Oc3cc(ccc23)O)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465365
PubChem CID:	497359
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	=	12000.0	nM	PMID[549916]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	2700.0	nM	PMID[549916]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Ki	=	11000.0	nM	PMID[549916]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Kis	=	8.2	uM	PMID[549916]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Kii	=	4.3	uM	PMID[549916]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	30.0	%	PMID[549916]

☑ 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 NPC178484 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	380
0.1-0.2	1457
0.2-0.3	3375
0.3-0.4	8495
0.4-0.5	10197
0.5-0.6	3526
0.6-0.7	5522
0.7-0.8	5438
0.8-0.85	2407
0.85-0.9	1185
0.9-0.95	598
0.95-1	117

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC121568
0.9664	High Similarity	NPC1796
0.9664	High Similarity	NPC257166
0.9653	High Similarity	NPC470131
0.9653	High Similarity	NPC470132
0.9653	High Similarity	NPC473078
0.9653	High Similarity	NPC470134
0.9653	High Similarity	NPC470133
0.9653	High Similarity	NPC109183
0.96	High Similarity	NPC51247
0.96	High Similarity	NPC15815
0.9592	High Similarity	NPC148945
0.9592	High Similarity	NPC78835
0.9592	High Similarity	NPC309512
0.9592	High Similarity	NPC316960
0.9592	High Similarity	NPC317715
0.9592	High Similarity	NPC204561
0.9589	High Similarity	NPC473016
0.9583	High Similarity	NPC470135
0.9583	High Similarity	NPC39045
0.9583	High Similarity	NPC473014
0.9583	High Similarity	NPC271288
0.9583	High Similarity	NPC235217
0.9583	High Similarity	NPC470136
0.9536	High Similarity	NPC195136
0.9536	High Similarity	NPC226462
0.9536	High Similarity	NPC42965
0.9536	High Similarity	NPC98023
0.953	High Similarity	NPC37253
0.953	High Similarity	NPC79375
0.9521	High Similarity	NPC145467
0.9517	High Similarity	NPC127059
0.9517	High Similarity	NPC285630
0.9517	High Similarity	NPC228779
0.9514	High Similarity	NPC125894
0.9514	High Similarity	NPC185276
0.9514	High Similarity	NPC85162
0.9514	High Similarity	NPC81697
0.9514	High Similarity	NPC223812
0.9514	High Similarity	NPC278249
0.9514	High Similarity	NPC107177
0.9514	High Similarity	NPC77794
0.947	High Similarity	NPC105584
0.9459	High Similarity	NPC476553
0.9459	High Similarity	NPC476551
0.9459	High Similarity	NPC476552
0.9456	High Similarity	NPC3642
0.9452	High Similarity	NPC473077
0.9452	High Similarity	NPC261271
0.9452	High Similarity	NPC300988
0.9452	High Similarity	NPC296998
0.9452	High Similarity	NPC10990
0.9452	High Similarity	NPC283234
0.9452	High Similarity	NPC308200
0.9452	High Similarity	NPC475348
0.9448	High Similarity	NPC197252
0.9448	High Similarity	NPC236766
0.9448	High Similarity	NPC473015
0.9448	High Similarity	NPC131568
0.9448	High Similarity	NPC473013
0.9448	High Similarity	NPC131579
0.9444	High Similarity	NPC66515
0.9444	High Similarity	NPC296917
0.9444	High Similarity	NPC32739
0.9444	High Similarity	NPC76372
0.9444	High Similarity	NPC166482
0.9444	High Similarity	NPC107572
0.9444	High Similarity	NPC324134
0.9444	High Similarity	NPC167624
0.9444	High Similarity	NPC166934
0.9444	High Similarity	NPC324436
0.9444	High Similarity	NPC194432
0.9444	High Similarity	NPC161506
0.9444	High Similarity	NPC265040
0.9444	High Similarity	NPC37496
0.9444	High Similarity	NPC40833
0.9444	High Similarity	NPC306829
0.9444	High Similarity	NPC228504
0.9444	High Similarity	NPC227579
0.9444	High Similarity	NPC220998
0.9444	High Similarity	NPC76338
0.9444	High Similarity	NPC64915
0.9444	High Similarity	NPC78
0.9444	High Similarity	NPC223500
0.9444	High Similarity	NPC10937
0.9444	High Similarity	NPC177354
0.9444	High Similarity	NPC182852
0.9444	High Similarity	NPC328164
0.9444	High Similarity	NPC1089
0.9444	High Similarity	NPC125855
0.9444	High Similarity	NPC148757
0.9412	High Similarity	NPC473012
0.9408	High Similarity	NPC121647
0.9404	High Similarity	NPC208258
0.9404	High Similarity	NPC322459
0.9404	High Similarity	NPC318527
0.9404	High Similarity	NPC475184
0.9404	High Similarity	NPC324358
0.9404	High Similarity	NPC323627
0.9396	High Similarity	NPC115601
0.9396	High Similarity	NPC78324
0.9396	High Similarity	NPC208011
0.9396	High Similarity	NPC43345
0.9396	High Similarity	NPC39154
0.9392	High Similarity	NPC471115
0.9392	High Similarity	NPC29777
0.9388	High Similarity	NPC160821
0.9388	High Similarity	NPC39195
0.9388	High Similarity	NPC122894
0.9388	High Similarity	NPC152233
0.9388	High Similarity	NPC132592
0.9384	High Similarity	NPC67805
0.9384	High Similarity	NPC176229
0.9384	High Similarity	NPC195621
0.9384	High Similarity	NPC476088
0.9384	High Similarity	NPC20488
0.9384	High Similarity	NPC472629
0.9384	High Similarity	NPC214774
0.9384	High Similarity	NPC142405
0.9384	High Similarity	NPC312973
0.9384	High Similarity	NPC267375
0.9384	High Similarity	NPC475052
0.9384	High Similarity	NPC246948
0.9384	High Similarity	NPC88964
0.9384	High Similarity	NPC474161
0.9384	High Similarity	NPC301276
0.9384	High Similarity	NPC83357
0.9384	High Similarity	NPC470647
0.9384	High Similarity	NPC54577
0.9384	High Similarity	NPC477955
0.9384	High Similarity	NPC111786
0.9379	High Similarity	NPC149026
0.9379	High Similarity	NPC310130
0.9379	High Similarity	NPC257097
0.9379	High Similarity	NPC150408
0.9379	High Similarity	NPC68104
0.9379	High Similarity	NPC175504
0.9379	High Similarity	NPC214166
0.9379	High Similarity	NPC91560
0.9379	High Similarity	NPC478086
0.9379	High Similarity	NPC75049
0.9379	High Similarity	NPC221432
0.9379	High Similarity	NPC143896
0.9379	High Similarity	NPC164980
0.9379	High Similarity	NPC316816
0.9379	High Similarity	NPC39329
0.9379	High Similarity	NPC169591
0.9375	High Similarity	NPC96408
0.9375	High Similarity	NPC248372
0.9375	High Similarity	NPC4743
0.9375	High Similarity	NPC17170
0.9375	High Similarity	NPC258630
0.9375	High Similarity	NPC156190
0.9375	High Similarity	NPC279650
0.9375	High Similarity	NPC312391
0.9375	High Similarity	NPC213322
0.9375	High Similarity	NPC110038
0.9375	High Similarity	NPC166689
0.9375	High Similarity	NPC324386
0.9351	High Similarity	NPC473009
0.9346	High Similarity	NPC312273
0.9346	High Similarity	NPC301256
0.9338	High Similarity	NPC32867
0.9338	High Similarity	NPC69531
0.9329	High Similarity	NPC312549
0.9329	High Similarity	NPC209142
0.9324	High Similarity	NPC471114
0.9324	High Similarity	NPC132345
0.932	High Similarity	NPC23728
0.932	High Similarity	NPC110303
0.9315	High Similarity	NPC87486
0.9315	High Similarity	NPC319752
0.9315	High Similarity	NPC311144
0.9315	High Similarity	NPC124780
0.9315	High Similarity	NPC209040
0.9315	High Similarity	NPC470890
0.931	High Similarity	NPC202981
0.9306	High Similarity	NPC76445
0.9306	High Similarity	NPC284550
0.9306	High Similarity	NPC6407
0.9306	High Similarity	NPC129853
0.9306	High Similarity	NPC110228
0.9306	High Similarity	NPC188243
0.929	High Similarity	NPC473010
0.9281	High Similarity	NPC114147
0.9276	High Similarity	NPC287789
0.9276	High Similarity	NPC271741
0.9272	High Similarity	NPC134171
0.9272	High Similarity	NPC66441
0.9272	High Similarity	NPC300668
0.9272	High Similarity	NPC182555
0.9267	High Similarity	NPC174086
0.9262	High Similarity	NPC472633
0.9257	High Similarity	NPC161191
0.9257	High Similarity	NPC35150
0.9257	High Similarity	NPC106328
0.9252	High Similarity	NPC24136
0.9252	High Similarity	NPC299011
0.9252	High Similarity	NPC290133
0.9252	High Similarity	NPC187282

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 NPC178484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	928
0.2-0.3	1441
0.3-0.4	2523
0.4-0.5	1994
0.5-0.6	1183
0.6-0.7	510
0.7-0.8	170
0.8-0.85	36
0.85-0.9	22
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9796	High Similarity	NPD8443	Clinical (unspecified phase)
0.9097	High Similarity	NPD1552	Clinical (unspecified phase)
0.9097	High Similarity	NPD1550	Clinical (unspecified phase)
0.9073	High Similarity	NPD7411	Suspended
0.9054	High Similarity	NPD7410	Clinical (unspecified phase)
0.9054	High Similarity	NPD4378	Clinical (unspecified phase)
0.9034	High Similarity	NPD1549	Phase 2
0.8961	High Similarity	NPD7768	Phase 2
0.8954	High Similarity	NPD7819	Suspended
0.8954	High Similarity	NPD2393	Clinical (unspecified phase)
0.8924	High Similarity	NPD7852	Clinical (unspecified phase)
0.8903	High Similarity	NPD7075	Discontinued
0.8882	High Similarity	NPD4380	Phase 2
0.8854	High Similarity	NPD6959	Discontinued
0.8831	High Similarity	NPD7096	Clinical (unspecified phase)
0.8767	High Similarity	NPD2796	Approved
0.8699	High Similarity	NPD1510	Phase 2
0.8645	High Similarity	NPD1934	Approved
0.8642	High Similarity	NPD7804	Clinical (unspecified phase)
0.8571	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD6166	Phase 2
0.8571	High Similarity	NPD6168	Clinical (unspecified phase)
0.8552	High Similarity	NPD1240	Approved
0.8544	High Similarity	NPD4381	Clinical (unspecified phase)
0.8542	High Similarity	NPD4907	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5494	Approved
0.8435	Intermediate Similarity	NPD1607	Approved
0.8428	Intermediate Similarity	NPD3749	Approved
0.8408	Intermediate Similarity	NPD6801	Discontinued
0.8403	Intermediate Similarity	NPD4908	Phase 1
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8289	Intermediate Similarity	NPD3750	Approved
0.8253	Intermediate Similarity	NPD7074	Phase 3
0.825	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD6799	Approved
0.8247	Intermediate Similarity	NPD1511	Approved
0.8239	Intermediate Similarity	NPD2801	Approved
0.8224	Intermediate Similarity	NPD2800	Approved
0.8193	Intermediate Similarity	NPD7054	Approved
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8188	Intermediate Similarity	NPD6651	Approved
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.8163	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7472	Approved
0.8141	Intermediate Similarity	NPD1512	Approved
0.8137	Intermediate Similarity	NPD3882	Suspended
0.811	Intermediate Similarity	NPD6232	Discontinued
0.8107	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7808	Phase 3
0.8079	Intermediate Similarity	NPD2799	Discontinued
0.8047	Intermediate Similarity	NPD7251	Discontinued
0.8047	Intermediate Similarity	NPD6559	Discontinued
0.8026	Intermediate Similarity	NPD6099	Approved
0.8026	Intermediate Similarity	NPD6100	Approved
0.8026	Intermediate Similarity	NPD1551	Phase 2
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7975	Intermediate Similarity	NPD5403	Approved
0.7974	Intermediate Similarity	NPD2344	Approved
0.7963	Intermediate Similarity	NPD3817	Phase 2
0.7962	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2533	Approved
0.7962	Intermediate Similarity	NPD2532	Approved
0.7962	Intermediate Similarity	NPD2534	Approved
0.7961	Intermediate Similarity	NPD3748	Approved
0.7955	Intermediate Similarity	NPD4363	Phase 3
0.7955	Intermediate Similarity	NPD4360	Phase 2
0.7917	Intermediate Similarity	NPD1610	Phase 2
0.7917	Intermediate Similarity	NPD3818	Discontinued
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7898	Intermediate Similarity	NPD7390	Discontinued
0.7882	Intermediate Similarity	NPD5953	Discontinued
0.7882	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1243	Approved
0.787	Intermediate Similarity	NPD7286	Phase 2
0.7865	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD920	Approved
0.7849	Intermediate Similarity	NPD8313	Approved
0.7849	Intermediate Similarity	NPD8312	Approved
0.7848	Intermediate Similarity	NPD5401	Approved
0.7843	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4628	Phase 3
0.7821	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2309	Approved
0.7764	Intermediate Similarity	NPD3226	Approved
0.7764	Intermediate Similarity	NPD7458	Discontinued
0.7763	Intermediate Similarity	NPD5124	Phase 1
0.7763	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5402	Approved
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD8455	Phase 2
0.7682	Intermediate Similarity	NPD2313	Discontinued
0.7682	Intermediate Similarity	NPD3268	Approved
0.7679	Intermediate Similarity	NPD7229	Phase 3
0.7667	Intermediate Similarity	NPD6832	Phase 2
0.7651	Intermediate Similarity	NPD2798	Approved
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7613	Intermediate Similarity	NPD7033	Discontinued
0.7611	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4361	Phase 2
0.7595	Intermediate Similarity	NPD7003	Approved
0.7584	Intermediate Similarity	NPD2797	Approved
0.7584	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7528	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7515	Intermediate Similarity	NPD7577	Discontinued
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD919	Approved
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5711	Approved
0.747	Intermediate Similarity	NPD1465	Phase 2
0.7468	Intermediate Similarity	NPD943	Approved
0.7452	Intermediate Similarity	NPD5408	Approved
0.7452	Intermediate Similarity	NPD5406	Approved
0.7452	Intermediate Similarity	NPD5404	Approved
0.7452	Intermediate Similarity	NPD5405	Approved
0.7451	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4287	Approved
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6355	Discontinued
0.7416	Intermediate Similarity	NPD8150	Discontinued
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7412	Intermediate Similarity	NPD1247	Approved
0.7407	Intermediate Similarity	NPD7447	Phase 1
0.7407	Intermediate Similarity	NPD8151	Discontinued
0.7405	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7394	Intermediate Similarity	NPD7584	Approved
0.7383	Intermediate Similarity	NPD1608	Approved
0.7383	Intermediate Similarity	NPD9717	Approved
0.738	Intermediate Similarity	NPD7870	Phase 2
0.738	Intermediate Similarity	NPD7871	Phase 2
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.7365	Intermediate Similarity	NPD5760	Phase 2
0.7365	Intermediate Similarity	NPD5761	Phase 2
0.7362	Intermediate Similarity	NPD6273	Approved
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3266	Approved
0.7351	Intermediate Similarity	NPD3267	Approved
0.7346	Intermediate Similarity	NPD7213	Phase 3
0.7346	Intermediate Similarity	NPD7212	Phase 2
0.7338	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD4749	Approved
0.733	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7696	Phase 3
0.7326	Intermediate Similarity	NPD7698	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7697	Approved
0.7321	Intermediate Similarity	NPD4288	Approved
0.7318	Intermediate Similarity	NPD8434	Phase 2
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD1201	Approved
0.7314	Intermediate Similarity	NPD1729	Discontinued
0.7312	Intermediate Similarity	NPD2654	Approved
0.7305	Intermediate Similarity	NPD6844	Discontinued
0.7299	Intermediate Similarity	NPD7177	Discontinued
0.7285	Intermediate Similarity	NPD3225	Approved
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD3972	Approved
0.7258	Intermediate Similarity	NPD6780	Approved
0.7258	Intermediate Similarity	NPD6781	Approved
0.7258	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD6778	Approved
0.7258	Intermediate Similarity	NPD6776	Approved
0.7258	Intermediate Similarity	NPD6782	Approved
0.7258	Intermediate Similarity	NPD6779	Approved
0.7246	Intermediate Similarity	NPD5890	Approved
0.7246	Intermediate Similarity	NPD5889	Approved
0.7239	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1470	Approved
0.7234	Intermediate Similarity	NPD7435	Discontinued
0.7232	Intermediate Similarity	NPD6104	Discontinued
0.7219	Intermediate Similarity	NPD2296	Approved
0.7212	Intermediate Similarity	NPD7427	Discontinued
0.7208	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.7197	Intermediate Similarity	NPD1933	Approved
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6234	Discontinued
0.7188	Intermediate Similarity	NPD6002	Phase 3
0.7188	Intermediate Similarity	NPD6006	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