NPASS Compound

Structure

NPC17968 OpenBabel07101718202D 34 36 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 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 4.3301 -3.5000 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 5.1962 1.0000 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 4.3301 -1.5000 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 4.3301 -4.5000 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 4.3301 1.5000 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 3.4641 -0.0000 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 5.1962 -0.0000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 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 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 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 -0.5000 0.0000 C 0 0 2 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 0.0000 -3.0000 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 1.7321 -0.0000 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 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 20 12 1 6 0 0 0 20 33 1 0 0 0 0 21 14 1 1 0 0 0 21 22 1 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 24 1 0 0 0 0 23 31 1 1 0 0 0 24 25 1 0 0 0 0 24 32 1 6 0 0 0 25 33 1 1 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.2
Volume:	475.944
LogP:	0.834
LogD:	0.765
LogS:	-2.148
# Rotatable Bonds:	11
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	3.912
Fsp3:	0.48
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:	-5.896
MDCK Permeability:	5.791514013253618e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.969
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	76.7978286743164%
Volume Distribution (VD):	0.617
Pgp-substrate:	10.814116477966309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.142
CYP2D6-substrate:	0.687
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	8.873
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.281
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.47
Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.153
Skin Sensitization:	0.796
Carcinogencity:	0.351
Eye Corrosion:	0.003
Eye Irritation:	0.11
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC17968

Natural Product ID:	NPC17968
*Common Name:**	Platyphylloside
IUPAC Name:	(5S)-1,7-bis(4-hydroxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-3-one
Synonyms:	Platyphylloside
Standard InCHIKey:	PVPDIJGSCANSAG-JSFAVJLPSA-N
Standard InCHI:	InChI=1S/C25H32O9/c26-14-21-22(30)23(31)24(32)25(34-21)33-20(12-6-16-3-9-18(28)10-4-16)13-19(29)11-5-15-1-7-17(27)8-2-15/h1-4,7-10,20-28,30-32H,5-6,11-14H2/t20-,21+,22+,23-,24+,25+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H](CC(=O)CCc2ccc(cc2)O)CCc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228449
PubChem CID:	9826264
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20363129]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15361	Alnus japonica	Species	Betulaceae	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
EC50	1
Others	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	16.7	%	PMID[559737]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	20.5	%	PMID[559737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	90.0	%	PMID[559735]
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	=	105000.0	nM	PMID[559736]
NPT27	Others	Unspecified		CC50	>	525000.0	nM	PMID[559736]
NPT2	Others	Unspecified		Ratio	>	5.0	n.a.	PMID[559736]

☑ 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 NPC17968 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	291
0.1-0.2	1105
0.2-0.3	2544
0.3-0.4	6842
0.4-0.5	11487
0.5-0.6	6515
0.6-0.7	10570
0.7-0.8	3143
0.8-0.85	155
0.85-0.9	25
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470122
1.0	High Similarity	NPC469705
0.984	High Similarity	NPC471066
0.984	High Similarity	NPC471095
0.9837	High Similarity	NPC158673
0.9762	High Similarity	NPC164172
0.9603	High Similarity	NPC476407
0.9462	High Similarity	NPC469696
0.9308	High Similarity	NPC103398
0.9308	High Similarity	NPC158325
0.9308	High Similarity	NPC180171
0.9187	High Similarity	NPC201402
0.9187	High Similarity	NPC469703
0.9187	High Similarity	NPC469704
0.9187	High Similarity	NPC160854
0.9113	High Similarity	NPC469686
0.904	High Similarity	NPC471067
0.9037	High Similarity	NPC148080
0.9037	High Similarity	NPC469623
0.8992	High Similarity	NPC469549
0.8968	High Similarity	NPC178449
0.8968	High Similarity	NPC470907
0.8968	High Similarity	NPC232454
0.8872	High Similarity	NPC123988
0.8806	High Similarity	NPC471345
0.8741	High Similarity	NPC302583
0.8741	High Similarity	NPC100558
0.8741	High Similarity	NPC84789
0.8741	High Similarity	NPC310252
0.8692	High Similarity	NPC264900
0.8692	High Similarity	NPC108659
0.8692	High Similarity	NPC79715
0.8692	High Similarity	NPC288416
0.8692	High Similarity	NPC231607
0.8692	High Similarity	NPC469687
0.8682	High Similarity	NPC123704
0.8661	High Similarity	NPC55608
0.8652	High Similarity	NPC473138
0.8652	High Similarity	NPC28776
0.8651	High Similarity	NPC469702
0.8651	High Similarity	NPC282409
0.8643	High Similarity	NPC212808
0.8629	High Similarity	NPC148055
0.8618	High Similarity	NPC157338
0.8615	High Similarity	NPC94179
0.8583	High Similarity	NPC476448
0.8583	High Similarity	NPC469548
0.8583	High Similarity	NPC476445
0.8571	High Similarity	NPC235294
0.8571	High Similarity	NPC46137
0.8571	High Similarity	NPC478255
0.8561	High Similarity	NPC184092
0.8561	High Similarity	NPC478250
0.8521	High Similarity	NPC116229
0.8519	High Similarity	NPC169398
0.8485	Intermediate Similarity	NPC225307
0.8451	Intermediate Similarity	NPC470330
0.8433	Intermediate Similarity	NPC246869
0.8433	Intermediate Similarity	NPC138777
0.8433	Intermediate Similarity	NPC225384
0.8433	Intermediate Similarity	NPC281798
0.8406	Intermediate Similarity	NPC62800
0.8406	Intermediate Similarity	NPC324262
0.8397	Intermediate Similarity	NPC83218
0.8397	Intermediate Similarity	NPC126991
0.8392	Intermediate Similarity	NPC120728
0.8374	Intermediate Similarity	NPC177576
0.837	Intermediate Similarity	NPC254275
0.8369	Intermediate Similarity	NPC296659
0.8369	Intermediate Similarity	NPC202391
0.8356	Intermediate Similarity	NPC259182
0.8356	Intermediate Similarity	NPC121001
0.8356	Intermediate Similarity	NPC87403
0.8346	Intermediate Similarity	NPC148982
0.8333	Intermediate Similarity	NPC65262
0.8333	Intermediate Similarity	NPC301651
0.8333	Intermediate Similarity	NPC175771
0.8333	Intermediate Similarity	NPC469364
0.8333	Intermediate Similarity	NPC473556
0.8333	Intermediate Similarity	NPC101686
0.8333	Intermediate Similarity	NPC471157
0.8333	Intermediate Similarity	NPC252114
0.8321	Intermediate Similarity	NPC263829
0.832	Intermediate Similarity	NPC313193
0.831	Intermediate Similarity	NPC475528
0.8308	Intermediate Similarity	NPC52097
0.8308	Intermediate Similarity	NPC469927
0.8299	Intermediate Similarity	NPC160882
0.8299	Intermediate Similarity	NPC106625
0.8293	Intermediate Similarity	NPC252544
0.8293	Intermediate Similarity	NPC321252
0.8288	Intermediate Similarity	NPC106818
0.8276	Intermediate Similarity	NPC12006
0.8276	Intermediate Similarity	NPC35097
0.8271	Intermediate Similarity	NPC106677
0.8264	Intermediate Similarity	NPC472339
0.8261	Intermediate Similarity	NPC472132
0.8252	Intermediate Similarity	NPC475539
0.8252	Intermediate Similarity	NPC291153
0.8252	Intermediate Similarity	NPC143246
0.8252	Intermediate Similarity	NPC119773
0.8252	Intermediate Similarity	NPC474268
0.8248	Intermediate Similarity	NPC886
0.8248	Intermediate Similarity	NPC287597
0.8248	Intermediate Similarity	NPC34293
0.8244	Intermediate Similarity	NPC236981
0.8243	Intermediate Similarity	NPC26195
0.8243	Intermediate Similarity	NPC72649
0.8243	Intermediate Similarity	NPC97052
0.8243	Intermediate Similarity	NPC131532
0.8243	Intermediate Similarity	NPC169248
0.8243	Intermediate Similarity	NPC99233
0.8243	Intermediate Similarity	NPC39351
0.8239	Intermediate Similarity	NPC194938
0.8231	Intermediate Similarity	NPC266045
0.8231	Intermediate Similarity	NPC259767
0.8231	Intermediate Similarity	NPC257847
0.8231	Intermediate Similarity	NPC88484
0.8231	Intermediate Similarity	NPC11724
0.8207	Intermediate Similarity	NPC287294
0.8201	Intermediate Similarity	NPC260425
0.8188	Intermediate Similarity	NPC127406
0.8188	Intermediate Similarity	NPC170475
0.8188	Intermediate Similarity	NPC206378
0.8176	Intermediate Similarity	NPC143851
0.8176	Intermediate Similarity	NPC83283
0.8176	Intermediate Similarity	NPC39360
0.8176	Intermediate Similarity	NPC210003
0.8176	Intermediate Similarity	NPC29763
0.8175	Intermediate Similarity	NPC28637
0.8175	Intermediate Similarity	NPC114116
0.8175	Intermediate Similarity	NPC285350
0.8154	Intermediate Similarity	NPC476872
0.8148	Intermediate Similarity	NPC253595
0.8148	Intermediate Similarity	NPC11025
0.8146	Intermediate Similarity	NPC246469
0.8146	Intermediate Similarity	NPC271270
0.8146	Intermediate Similarity	NPC208676
0.8146	Intermediate Similarity	NPC97285
0.8146	Intermediate Similarity	NPC130489
0.8146	Intermediate Similarity	NPC142860
0.8143	Intermediate Similarity	NPC321184
0.8143	Intermediate Similarity	NPC171134
0.8143	Intermediate Similarity	NPC321638
0.8143	Intermediate Similarity	NPC81515
0.8143	Intermediate Similarity	NPC197316
0.8143	Intermediate Similarity	NPC68092
0.8143	Intermediate Similarity	NPC64141
0.8143	Intermediate Similarity	NPC89105
0.8143	Intermediate Similarity	NPC328273
0.8143	Intermediate Similarity	NPC472350
0.8143	Intermediate Similarity	NPC205195
0.8143	Intermediate Similarity	NPC476383
0.8134	Intermediate Similarity	NPC35288
0.8134	Intermediate Similarity	NPC471881
0.8134	Intermediate Similarity	NPC471882
0.8134	Intermediate Similarity	NPC156692
0.8134	Intermediate Similarity	NPC173150
0.8134	Intermediate Similarity	NPC45224
0.8133	Intermediate Similarity	NPC197896
0.8133	Intermediate Similarity	NPC6985
0.8133	Intermediate Similarity	NPC43638
0.8133	Intermediate Similarity	NPC313163
0.8133	Intermediate Similarity	NPC258035
0.8133	Intermediate Similarity	NPC161749
0.8133	Intermediate Similarity	NPC23817
0.8133	Intermediate Similarity	NPC156457
0.8133	Intermediate Similarity	NPC177742
0.8129	Intermediate Similarity	NPC177035
0.8129	Intermediate Similarity	NPC199459
0.8129	Intermediate Similarity	NPC52277
0.8125	Intermediate Similarity	NPC474465
0.8125	Intermediate Similarity	NPC473147
0.8121	Intermediate Similarity	NPC95090
0.8121	Intermediate Similarity	NPC27408
0.812	Intermediate Similarity	NPC90318
0.812	Intermediate Similarity	NPC127975
0.8116	Intermediate Similarity	NPC471029
0.8112	Intermediate Similarity	NPC471028
0.8112	Intermediate Similarity	NPC63304
0.811	Intermediate Similarity	NPC23402
0.8108	Intermediate Similarity	NPC245615
0.8108	Intermediate Similarity	NPC61604
0.8108	Intermediate Similarity	NPC299706
0.8108	Intermediate Similarity	NPC115466
0.8099	Intermediate Similarity	NPC296643
0.8099	Intermediate Similarity	NPC65833
0.8095	Intermediate Similarity	NPC474620
0.8082	Intermediate Similarity	NPC96599
0.8082	Intermediate Similarity	NPC478242
0.8079	Intermediate Similarity	NPC473634
0.8079	Intermediate Similarity	NPC469654
0.8079	Intermediate Similarity	NPC22062
0.8079	Intermediate Similarity	NPC308265
0.8079	Intermediate Similarity	NPC73511
0.8079	Intermediate Similarity	NPC138811
0.8077	Intermediate Similarity	NPC265454
0.8077	Intermediate Similarity	NPC34634
0.8071	Intermediate Similarity	NPC78363
0.8067	Intermediate Similarity	NPC265480

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 NPC17968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	732
0.2-0.3	1387
0.3-0.4	2748
0.4-0.5	2244
0.5-0.6	1259
0.6-0.7	490
0.7-0.8	47
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8143	Intermediate Similarity	NPD7266	Discontinued
0.8133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD8455	Phase 2
0.7785	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7074	Phase 3
0.7733	Intermediate Similarity	NPD4380	Phase 2
0.7673	Intermediate Similarity	NPD7054	Approved
0.7625	Intermediate Similarity	NPD7472	Approved
0.761	Intermediate Similarity	NPD3818	Discontinued
0.7556	Intermediate Similarity	NPD1091	Approved
0.7552	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6190	Approved
0.7531	Intermediate Similarity	NPD7251	Discontinued
0.7531	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7469	Intermediate Similarity	NPD6797	Phase 2
0.7436	Intermediate Similarity	NPD7075	Discontinued
0.7397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6233	Phase 2
0.7391	Intermediate Similarity	NPD7228	Approved
0.7378	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1549	Phase 2
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD8312	Approved
0.7324	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD37	Approved
0.729	Intermediate Similarity	NPD1934	Approved
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7261	Intermediate Similarity	NPD4965	Approved
0.7261	Intermediate Similarity	NPD4967	Phase 2
0.7261	Intermediate Similarity	NPD4966	Approved
0.726	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD3400	Discontinued
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7244	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7097	Phase 1
0.719	Intermediate Similarity	NPD5403	Approved
0.7188	Intermediate Similarity	NPD5048	Discontinued
0.7179	Intermediate Similarity	NPD6801	Discontinued
0.7172	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5125	Phase 3
0.7153	Intermediate Similarity	NPD5126	Approved
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7108	Intermediate Similarity	NPD7685	Pre-registration
0.7103	Intermediate Similarity	NPD1613	Approved
0.7103	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2859	Approved
0.7097	Intermediate Similarity	NPD2860	Approved
0.7089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD5401	Approved
0.7059	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5058	Phase 3
0.7034	Intermediate Similarity	NPD6663	Approved
0.7034	Intermediate Similarity	NPD4062	Phase 3
0.7032	Intermediate Similarity	NPD1653	Approved
0.7016	Intermediate Similarity	NPD2933	Approved
0.7016	Intermediate Similarity	NPD2934	Approved
0.7007	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD7240	Approved
0.7006	Intermediate Similarity	NPD7411	Suspended
0.6993	Remote Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD5736	Approved
0.6986	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1240	Approved
0.6986	Remote Similarity	NPD943	Approved
0.6981	Remote Similarity	NPD5402	Approved
0.6975	Remote Similarity	NPD7199	Phase 2
0.697	Remote Similarity	NPD3751	Discontinued
0.6963	Remote Similarity	NPD2629	Approved
0.6954	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7843	Approved
0.6929	Remote Similarity	NPD1535	Discovery
0.6929	Remote Similarity	NPD3020	Approved
0.6929	Remote Similarity	NPD1201	Approved
0.6923	Remote Similarity	NPD5647	Approved
0.6918	Remote Similarity	NPD2801	Approved
0.6918	Remote Similarity	NPD7819	Suspended
0.6908	Remote Similarity	NPD8166	Discontinued
0.6908	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3019	Approved
0.6906	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2932	Approved
0.6899	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1607	Approved
0.6884	Remote Similarity	NPD1894	Discontinued
0.6883	Remote Similarity	NPD1511	Approved
0.6879	Remote Similarity	NPD1481	Phase 2
0.6879	Remote Similarity	NPD7458	Discontinued
0.6875	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD3817	Phase 2
0.6867	Remote Similarity	NPD2935	Discontinued
0.6867	Remote Similarity	NPD9570	Approved
0.6867	Remote Similarity	NPD2796	Approved
0.6859	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6534	Approved
0.6857	Remote Similarity	NPD6535	Approved
0.6853	Remote Similarity	NPD1470	Approved
0.6853	Remote Similarity	NPD3094	Phase 2
0.6846	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4536	Approved
0.6846	Remote Similarity	NPD4538	Approved
0.6842	Remote Similarity	NPD3021	Approved
0.6842	Remote Similarity	NPD3022	Approved
0.6842	Remote Similarity	NPD6674	Discontinued
0.6839	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7700	Phase 2
0.6836	Remote Similarity	NPD7699	Phase 2
0.6835	Remote Similarity	NPD6599	Discontinued
0.6828	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4908	Phase 1
0.6821	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1610	Phase 2
0.6809	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2798	Approved
0.6806	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5588	Approved
0.68	Remote Similarity	NPD5960	Phase 3
0.6797	Remote Similarity	NPD3750	Approved
0.6795	Remote Similarity	NPD1512	Approved
0.6788	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7157	Approved
0.6781	Remote Similarity	NPD7095	Approved
0.6778	Remote Similarity	NPD6823	Phase 2
0.6767	Remote Similarity	NPD2684	Approved
0.6763	Remote Similarity	NPD1548	Phase 1
0.676	Remote Similarity	NPD6780	Approved
0.676	Remote Similarity	NPD6779	Approved
0.676	Remote Similarity	NPD6777	Approved
0.676	Remote Similarity	NPD6782	Approved
0.676	Remote Similarity	NPD6781	Approved
0.676	Remote Similarity	NPD6778	Approved
0.676	Remote Similarity	NPD6776	Approved
0.6759	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5408	Approved
0.6755	Remote Similarity	NPD5406	Approved
0.6755	Remote Similarity	NPD5404	Approved
0.6755	Remote Similarity	NPD5405	Approved
0.6746	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7435	Discontinued
0.6738	Remote Similarity	NPD3847	Discontinued
0.6736	Remote Similarity	NPD2797	Approved
0.6736	Remote Similarity	NPD1164	Approved
0.6735	Remote Similarity	NPD3268	Approved
0.6735	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7768	Phase 2
0.6728	Remote Similarity	NPD3882	Suspended
0.6721	Remote Similarity	NPD7584	Approved
0.6719	Remote Similarity	NPD9495	Approved
0.6718	Remote Similarity	NPD1237	Approved
0.6713	Remote Similarity	NPD4659	Approved
0.6713	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6832	Phase 2
0.6711	Remote Similarity	NPD230	Phase 1
0.6711	Remote Similarity	NPD1933	Approved
0.6711	Remote Similarity	NPD4340	Discontinued
0.6707	Remote Similarity	NPD7473	Discontinued
0.6705	Remote Similarity	NPD8150	Discontinued
0.6705	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6212	Phase 3
0.6705	Remote Similarity	NPD6213	Phase 3
0.6703	Remote Similarity	NPD8319	Approved
0.6703	Remote Similarity	NPD8320	Phase 1
0.6692	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD940	Approved
0.6692	Remote Similarity	NPD846	Approved
0.669	Remote Similarity	NPD3092	Approved
0.6689	Remote Similarity	NPD6405	Approved
0.6689	Remote Similarity	NPD6407	Approved
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD5846	Approved
0.6667	Remote Similarity	NPD6516	Phase 2
0.6667	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD5958	Discontinued
0.6667	Remote Similarity	NPD6653	Approved
0.6648	Remote Similarity	NPD7698	Approved
0.6648	Remote Similarity	NPD7696	Phase 3
0.6648	Remote Similarity	NPD7697	Approved
0.6647	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1551	Phase 2
0.6645	Remote Similarity	NPD6100	Approved
0.6645	Remote Similarity	NPD6099	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